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Join us in delivering our industry-leading pharmacy care to millions of people across the country. As a member of the team, you’ll play an integral role in improving our customers’ quality of life and redefining what’s possible in pharmacy. 

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Blog | Alto Pharmacy

When Jake Moffatt says he loves building things, he means it — sometimes literally. A construction project manager turned engineer, Jake has spent the past decade building software at mission-driven organizations. Today, as Engineering Manager of Alto Assistant, he leads the team that’s bringing wizard-like support to Alto’s customer-facing app.

Get to know Jake Moffatt, Engineering Manager on the Alto Assistant Team

When Jake Moffatt says he loves building things, he means it — sometimes literally. A construction project manager turned engineer, Jake has spent the past decade building software at mission-driven organizations. Today, as Engineering Manager of Alto Assistant, he leads the team that’s bringing wizard-like support to Alto’s customer-facing app.
Below, Jake chats with fellow engineering manager Mike Riess and recruiter Braden Hanlon about the work ahead for Alto Assistant.

I’d love to learn more about your background to get us started. How did you end up in software engineering?

When I was twelve, I started learning to code in QBASIC because I wanted to make video games. Once I wrote my first program, I was hooked! I loved computers and the creative power they gave to anyone willing to invest the time and energy to learn. Since then, I’ve built games, personal tools and projects, desktop software, and a number of apps and services — I love building things. My career has gone back and forth between construction and software engineering, but it’s been firmly in the software industry for the last ten years or so.

My favorite place to be in a company is working on something new that has a big impact or addresses an important problem. In a previous role, I built an app that helped people find roommates in a city where housing is prohibitively expensive. At that same company, I led the team responsible for creating a new vertical that eventually split off into its own company.

The goal of Alto Assistant is to help customers help themselves before reaching out to support. Our first project is introducing a wizard-like support “assistant” (hence the team name!) that guides the customer through a series of questions to narrow down the area of support. We’ve already identified a few tasks the assistant can help customers complete on their own, including making changes to upcoming deliveries or scheduling new orders.

In cases where we can’t help them just yet, our new tool generates data to help us to learn exactly what customers need help with. It’s a top priority to bake analytics into every new feature we build; even though we have years of experience supporting our customers — and we know intuitively which problems they frequently experience — we don’t have conclusive data to draw upon just yet.

We plan to start with a couple of frequent use cases and measure how often customers reach out to us for support. Then, we’ll chip away at the problem until we’ve seen a substantial improvement in the user experience. From there, we’ll move on to the next biggest problem and repeat the cycle. There’s a reason “Chip away it” is an Alto value: It’s the playbook that we’ve used to automate other critical parts of the pharmacy value stream like intake, billing, and fulfillment.

What opportunities are you most excited about?

Support drives much of the cost of every shipment today, so this is a high-impact area for our business. A year from now, it would be a stellar outcome if the Assistant team could reduce the number of issues that customers need support on by half.

We’re also thinking about the user experience beyond the app. We plan to improve the tooling that our care specialists use to provide support as well. We’ve already discussed some promising ideas like creating the concept of a conversation in support communications rather than an infinite stream of messages and building out enriched communications. We also intend to develop a custom tool that can expedite a customer’s prescription when they need their medication ASAP.

The possibilities are many, and it will take a team of determined, passionate, empathetic people to solve these challenging problems. I’m super excited to see what the Assistant team will do together.

Any lessons learned from previous experience that you’re applying to your role at Alto?

There’s always the temptation to tackle everything at once with new business initiatives. My experience leading new verticals at Apartment List and Snapdocs taught me the importance of being laser-focused on one or two key metrics instead of trying to build out a fully-realized product from the beginning. That’s exactly what we’re doing on the Alto Assistant Team with our clear focus on reducing communications per shipment — how often customers reach out for help because they could not find what they needed in our app.

It’s also important to recognize that we won’t have all the answers right out of the gate! I like to think of product development as a three-step sequence: learning, growth, and maintenance. Alto Assistant is so young that we’re very much still in the learning phase. We maintain a tight iteration loop with everything we ship: launch, measure the impact, and use the results to iterate and refine our hypotheses about what our users want. Our final product could be anything from a customer support wizard to an AI chatbot to a ticketing system — we have to rely on our key metric of communications per shipment, experimentation, and user feedback to shape the direction.

What got you excited to join Alto? What would you pass on to an engineer thinking about applying to the company?

I was impressed by the Altoids I met during the interview process. I knew I would be working with people from whom I could learn a lot, like Elnaz, who started as an individual contributor and went on to become Director of Engineering and, now, Alto’s first Head of Strategy & Operations. I was also impressed by the quality of the interview process itself — a good sign that the company was well-organized internally. Finally, the pitch for the role was extremely clear, with already-established key metrics that would directly contribute to the company’s bottom line and help Alto become more profitable.

For engineers, I think Alto is a great place for both technical challenges and career growth. We’re still small enough that every individual gets exposure to a broad portfolio of high-impact projects. It’s also a great environment for learning about how a business works — the Product & Technology organization does a great job of sharing information and presenting problems in a way that gets to the root business problem we’re trying to solve. There’s a clear line between any project a team is working on and a foundational business metric. Most importantly, we’re a company that makes a truly positive impact on our users’ lives.

Interested in learning more about engineering at Alto? Follow us on LinkedIn.

Alto’s board of advisors was formed in 2020 to deliver strategic guidance as we work toward a better healthcare system for all. With diverse leadership experience in the industry, our board of advisor members ensure that our efforts are both impactful and efficient, with services grounded in the highest standards of operational excellence.

Meet the Newest Members of our Advisory Board | Alto Pharmacy

Today we’re thrilled to welcome three new members to the board of advisors: Adam J. Fein, Harry Leider, and Brad Fluegel. Their passion and expertise will no doubt be an asset as we focus on reaching even more patients — and delivering even more comprehensive care — in service of our mission.

Read on to learn more about their backgrounds in the industry and join us in giving them a warm welcome!

Adam J. Fein, PhD, is the CEO of Drug Channels Institute, a leading source of industry research about pharmaceutical economics and the drug distribution system. Widely published in academic and industry publications, he also heads the Drug Channels website, praised by readers for its comprehensive and witty coverage of pharmacy benefit managers (PBMs), medication pricing, and other industry topics.

Delivering medications to our patients at the lowest price possible is central to our mission. Dr. Fein’s deep expertise in pharmacy economics supports our ongoing commitment to improve adherence rates by way of more affordable medication options and total price transparency.

“The pharmacy industry has entered a period of structural change. There’s a tremendous need for the cost transparency, efficiency, and commitment to patient well-being that Alto delivers. I’m thrilled to support Alto in building innovative solutions to foundational issues within the industry,” Dr. Fein said.

Dr. Fein holds a doctoral degree in managerial science and applied economics from the University of Pennsylvania’s Wharton School of Business.

Harry L. Leider, MD, MBA brings more than 25 years of experience as a senior healthcare executive to our board of advisors. Since 2018, he’s served as Chief Medical Officer and Executive Vice President of Gelesis, an innovative biopharmaceutical company.

In addition to his current leadership in the biotherapeutic space, Dr. Leider has broad experience in telemedicine, retail healthcare, laboratory medicine, and payor strategies, as former Chief Medical Officer of Walgreens Boots Alliance, Ameritox, and Care Improvement Plus.

Dr. Leider shares Alto’s commitment to driving lasting change within the healthcare system for better patient health. With both clinical expertise and executive experience, he’s spent his career designing programs, services, and intellectual property that improve health outcomes.

“Alto’s pharmacy model brings us closer to a future where everyone can receive the highest standard of care and is equipped to manage their health. I’m personally inspired by Alto’s bold vision for healthcare and look forward to what we can accomplish together,” Dr. Leider said.

Dr. Leider has served on the faculty of Harvard Medical School and the Johns Hopkins Carey School of Business and holds five patents in laboratory medicine.

Drawing on more than three decades of healthcare experience, Brad Fluegel is a strategic advisor to organizations, entrepreneurs, and other industry participants. Most recently he served as Senior Vice President and Chief Healthcare Commercial Market Development Officer for Walgreen Co, where he managed all commercial healthcare activities, from sales and contracting to biopharma relationships and market planning.

Previously, Brad oversaw Walgreens’ corporate strategy and business development as Chief Strategy and Business Development Officer. He also led Elevance (then Wellpoint)’s strategic planning and corporate communications as Executive Vice President and Chief Strategy and External Affairs Officer.

His expertise in strategic planning and operations will allow us to deliver an exceptional patient experience as we continue to grow.

“Since 2015, Alto has proven itself to be a leader in the rapidly evolving digital pharmacy space. It’s a privilege to support their efforts to redefine what’s possible in healthcare, and together we can deliver industry-leading care to more patients,” he said.

Brad earned a master’s degree in public policy from Harvard University’s Kennedy School of Government and a bachelor of arts in business administration from the University of Washington. He also serves as a lecturer at the Wharton School of Business.

Dr. Fein, Dr. Leider, and Brad join three other advisory board members: Dr. James Hildreth, the President and Chief Executive Officer of Meharry Medical College; Jennifer Kent, previously the Director for the California Department of Health Care Services; and Ajay Khatri, previously Alto’s Chief Strategy Officer. 

Dr. Hildreth, Jennifer, and Ajay have offered invaluable guidance as we’ve grown throughout the past two years, and we couldn’t be more grateful for their partnership and support.

Learn more about Dr. Hildreth and Jennifer’s healthcare experience.

Visit alto.com/careers to learn more about our open roles and join us in delivering industry-leading pharmacy care.

This content is not intended to be a substitute for professional medical advice, diagnosis, or treatment. Always seek the advice of your physician or another qualified health provider with any questions you may have regarding a medical condition.

Meet the Newest Members of Our Advisory Board

Redux is great for managing client state: it allows data to be synchronized across the whole app, reduces prop drilling, and makes it easier to understand when state changes occur.

Server state is a different story. Sure, it’s nice to have data available everywhere in our app, which is why we tend to fetch data from the server and dump it into our Redux store. But because our client application doesn't own that server data, it’s hard to know when it has become stale. And what if multiple components trigger calls to fetch the same data? How do you dedupe requests? How do you decide when to refetch?

Why We Switched to React Query for Managing Server State

Redux is great for managing client state: it allows data to be synchronized across the whole app, reduces prop drilling, and makes it easier to understand when state changes occur.

Server state is a different story. Sure, it’s nice to have data available everywhere in our app, which is why we tend to fetch data from the server and dump it into our Redux store. But because our client application doesn't own that server data, it’s hard to know when it has become stale. And what if multiple components trigger calls to fetch the same data? How do you dedupe requests? How do you decide when to refetch?

Below, we’ll dive into how we’re using React Query at Alto to solve these problems and achieve separation of client and server state.

The Old Way: Fetch Server Data and Store It in State

Historically, we would fetch data and set the response in our React component state.

fetchUser(params) {
 this.setState({ isLoading: true });
 
 return getUser(params)
   .then(({ data }) => {
     this.setState({
       isLoading: false,
       user: data.user,
     });
   })
   .catch(() => {
     toaster.toast({ title: 'Something went wrong...' });
     this.setState({ isLoading: false });
   });
}

To make that data accessible from other components, we’d set that data in the global Redux store. This works fine, except that you have to manage your own loading state, the logic for when and when not to make the request, updating the store when mutating data on the server, and knowing when data is stale.

The React Query Way: Fetch and Cache Server Data

With React Query, fetching data and using that data is more declarative.

const { data, error, isLoading } = useQuery(
 // This is our Query Key, which is unique per query so that React
 // Query can manage the cache for us.
 ['user', { userId }],
 
 // This is our Query Function that actually does the data fetching.
 // We can use anything we want: built-in fetch, axios, etc.
 fetchUser({ userId }),
 
 // This query will not execute until the userId exists.
 { enabled: !!userId },
);

Here, we define our query for a user with a Query Key and a Query Function. The Query Key is unique per query, so React Query can manage our cache for us, and if any part of the Query Key changes, the query will automatically fetch new data. In this example, if the user ID changes, the query will fetch new data for that specific user and store that data in the cache.

Naming is hard, but caching is harder. React Query gives us caching of server data out of the box with cache invalidation and request deduping. If we use this same query with the same Query Key in another component, it'll check the cache: if the data is already there, React Query will simply return it, avoiding extra network requests!

Additionally, useQuery runs wherever you use it — no more fetching data when a component mounts. You just use the query and display the data when it’s ready. The cherry on top? The query returns status updates by default, so we don’t need to store isLoading in component state all the time.

Three Optimizations We Get With React Query

When we rebuilt Alto Connect, our web app for healthcare providers, we found impactful benefits in using React Query to help us manage server state instead of using Redux. Alto Connect provides instant access to patient and prescription information and enables messaging with the pharmacy. Because healthcare providers need to quickly switch between patients and clinics, caching data is important to provide a delightfully fast experience. Apart from the cache, what other optimizations do we get by using React Query? Below are a few that helped us.

Once we’ve queried for some data, it gets entered into our cache, so we can utilize that cached data when using the same query in a different component or when fetching new data for a stale query in the background.

React Query is configured with aggressive but sane defaults and considers cached data as stale. Stale queries will always query for new data when the following criteria are met:

The query is optionally configured with a refetch interval

The fetching for new data when the browser window or tab is refocused is especially useful because the healthcare providers using Alto Connect often switch between multiple browser tabs. If there’s an update to a task, status, or message while they’re checking a patient’s medical chart, it will be immediately reflected in the UI when they come back to Alto Connect.

We also set a refetch interval for our queries involving messages. In the old app, we used WebSockets to enable real-time messaging. Although it’s possible to integrate WebSockets with React Query, we opted for a polling solution instead. Because our app isn’t a real-time messaging application, and we don’t need messages to show up immediately, we set a refetch interval on our messages query to poll for new messages every 30 seconds.

const { data, error, isLoading } = useQuery(
 ['user', { userId }, 'messages'],
 fetchMessages({ userId }),
 {
   // This query is disabled from automatically running if we don’t have a userId
   enabled: !!userId,
 
   // Refetch every 30 seconds
   refetchInterval: 30000,
 
   // Continue to refetch while the tab/window is in the background
   refetchIntervalInBackground: true,
 },
);

This is where the enabled option, which disables a query when it evaluates to false, is particularly powerful. We can pause polling for messages if we route to another page and we know that we won’t make any unnecessary requests if there isn’t a valid userId. We don’t have to worry about closing any socket connections or manually clearing an interval.

Most web apps have some sort of navigation menu, and if you already measure or understand your user behavior, you can prefetch data before users even navigate to a different page. Custom hooks makes it easy to expose a function to prefetch data:

export const usePrefetchUsers = () => {
 const queryClient = useQueryClient();
 const prefetchUsers = async () => {
   await queryClient.prefetchQuery(
     ['users'],
     fetchUsers,
   );
 };
 
 return { prefetchUsers };
};

We prefetch queries when users mouseover or hover over a navigation item so that when they navigate to the next page, the data is either actively being fetched or is already in the cache waiting.

We’ve been talking a lot about queries, but what about mutating data? Mutations, in contrast to queries, are imperative. While queries run automatically when we use them, we need to fire a mutation method in order to run mutations. And in order for our user experience to feel snappy, we can optimistically update the cache and then invalidate it after successfully executing the mutation. useMutation gives us some nice side-effect handlers to deal with every stage of the mutation lifecycle. Now when the user sends a message, that new message is immediately reflected in the UI and we keep the data in sync by invalidating the cache and refetching the messages.

With Redux, we needed to build out solutions to each challenge of managing server state. React Query, on the other hand, gives us those tools right out of the box. We no longer need to worry about when to invalidate or fetch new data, making the user experience more predictable — and the developer experience more enjoyable.

Last summer, Moringa Fellows Irma Figueroa and Adrian Mendez joined Alto as the company’s second batch of engineering interns. Here, they share their learnings, accomplishments, and advice for future Alto interns.

Two Engineering Interns Weigh In: What to Expect From Your Alto Internship

The Moringa tree flourishes almost anywhere it’s planted. It’s hardy, fast-growing, and resistant to drought — an apt metaphor for the two interns who joined us from the Moringa Fellowship program last summer.

“Before Alto, I had never actually contributed to a large codebase,” admits Irma Figueroa, an intern on the Supply Chain Team. By the end of their three-month internships, however, Irma and fellow intern Adrian Mendez had shipped impactful features for Alto’s internal pharmacy management system and customer-facing app that are still in production today.

Below, we chat with Irma and Adrian to learn what it was like interning at Alto, which projects they worked on, and what advice they’d give to future interns. 

Adrian, who interned on the Patients Team before returning to join as a full-time software engineer last fall, was surprised by the freedom he had to choose what he worked on during his internship: “Early on, my manager gave me a rundown of the projects the team was juggling and the option to choose which one interested me the most,” he says. “I was able to decide the kind of experience I was going to have.” 

Adrian adds that meetings with his mentor evolved over the course of his internship, as he became more familiar with the codebase: “From the start, we had weekly meetings to talk about whatever was on my mind. Those meetings started off as general advice and questions and turned into more time to pair or run things by each other.”

Because both Adrian and his mentor were working on the same, long-term project, some of those meetings were also dedicated to project work. This included “sitting with [my mentor] while creating the project outline, pairing on larger tasks, and syncing up on progress.” 

Which projects did you work on during your internship? 

On the Supply Chain Team, Irma was tasked with a unique inventory challenge: Technicians at our production pharmacy locations use handheld scanners to scan the barcodes on newly-received inventory. Our technicians often need to scan hundreds of inventory items at a time — making it all too easy to lose track of which items have been successfully scanned onto which shelves. 

“I created a reusable counter component, displayed in the header of the scanner app, that would represent the number of items scanned into a shelf.” Irma says. The best part? Getting to test the handheld scanner herself. “I really enjoyed using the scanner for testing purposes. It was rewarding to see my code in action and definitely super fun!” 

On the Patients Team, Adrian worked on a project to add a homescreen to the customer-facing native app. Previously, the app dropped users into a list of all their active medications, which made it difficult to know where to look or what to do next. The new homescreen allows users to schedule the prescriptions most relevant to them and to view or edit any upcoming deliveries. 

“The first step was to create new additions to the design system — essentially taking the designs and extracting system-wide components. After that, the fun part was taking all those components and putting them together like building blocks!” Adrian says.

It was especially rewarding, he adds, to have been part of the project from start to finish. “I joined right as the design phase started, and I was there mostly every step of the way. For how short my time here was, having helped create this landmark project is really cool to think about.” 

What advice would you give to future Alto interns?

Irma and Adrian agree: Don’t be afraid to ask for help. “You'll often feel challenged and possibly intimidated, but be patient with yourself and remember you have an entire team of experienced engineers ready to help,” Irma says. 

“Everyone at Alto is more than willing to help you out, so don't be afraid to ask questions! You're on the same ship as everyone else, so your success equals everyone’s success,” Adrian adds. “Just remember that your work got you here, and they wouldn't have invited you if they thought you couldn't handle it. They made an investment in your ability to grow, so stay curious.” 

Interested in interning at Alto? Check out our careers page here.

Alto’s mission is to improve the quality of life for all who need medicine, building a pharmacy experience that serves people of all backgrounds. As we work toward a more inclusive and accessible healthcare system, we recognize the importance of diversity among physicians, pharmacists, nurses, and other public health figures. In honor of Black History Month, take a moment to learn about five influential Black healthcare leaders past and present — those who paved the way and those who continue to break barriers today

Five Black Healthcare Leaders to Celebrate

Alto’s mission is to improve the quality of life for all who need medicine, building a pharmacy experience that serves people of all backgrounds. As we work toward a more inclusive and accessible healthcare system, we recognize the importance of diversity among physicians, pharmacists, nurses, and other public health figures. In honor of Black History Month, take a moment to learn about five influential Black healthcare leaders past and present — those who paved the way and those who continue to break barriers today. (For additional inspiration, revisit the first post in this series.)

Dr. M. Jocelyn Elders: the first Black U.S. surgeon general

As a Black woman born to farmers in a rural, poverty-stricken area of Arkansas, M. Jocelyn Elders encountered numerous obstacles on her path to becoming the first Black U.S. Surgeon General in 1993. At 16, she met a doctor for the first time, but she didn't consider a profession in healthcare until she connected with Edith Irby Jones, the first Black person to attend the University of Arkansas Medical School, during college.

Throughout her career, Dr. Elders balanced clinical practice and research, increasing the public’s awareness of adolescent health issues. In 1987, Bill Clinton, then the governor of Arkansas, appointed Dr. Elders as head of the state’s Department of Health. The Arkansas state legislature mandated sexual education and substance misuse prevention programs in the K-12 curriculum in 1989 in large part because of Dr. Elders’ advocacy. During her tenure as Surgeon General, Dr. Elders continued to champion progressive policies, advocating for better sexual education programs, distribution of condoms in schools, and abortion rights. She remains active in the field of public health as a professor emeritus at the University of Arkansas School of Medicine.

Bernard J. Tyson: former CEO of Kaiser Permanente

As chairman and CEO of Kaiser Permanente, Bernard Tyson transformed the company’s services to account for social determinants of health like food access and affordable housing as well as the importance of mental health and wellness. He was also instrumental in the development of the Kaiser Permanente School of Medicine, which trains physicians to be not only clinicians, but patient advocates and innovators, too. By shining a spotlight on how social determinants of health contribute to disparities in health outcomes, Tyson leaves behind a legacy that reaches far beyond Kaiser’s services.

Nadine Burke Harris: first surgeon general of California

A physician, researcher, advocate, and California’s first surgeon general, Dr. Nadine Burke Harris has transformed how our society responds to childhood trauma. While running a health clinic in an underserved San Francisco neighborhood, she observed that preventative health practices and quality treatment didn’t resolve her patients’ risk for poor health outcomes. Drawing upon research from the CDC and Kaiser Permanente on adverse childhood experiences (ACEs), which linked early adversity to higher rates of chronic illness later in life, Dr. Burke Harris studied her own patients and found that more than 67% had experienced at least one ACE. She has helped increase public awareness of ACEs and toxic stress, advocating for universal screening of children and adolescents for signs of trauma. Her 2014 TED Talk, “How Childhood Trauma Affects Health Across the Lifetime,” has been viewed more than 7.5 million times, and she published The Deepest Well: Healing the Long-Term Effects of Childhood Adversity in 2018.

Dr. Patrice Harris: first Black female president of the American Medical Association

Despite not knowing any doctors while growing up in West Virginia, Dr. Patrice Harris’ passion for medicine started early. The board-certified psychiatrist initially planned to pursue pediatrics but shifted her focus after discovering an interest in psychiatry during medical school. Her focus on child psychiatry allows her to merge her passion for children with her expertise in mental health. Throughout her career, Dr. Harris has focused on the role of implicit bias within the medical profession and how unconscious biases among healthcare workers influence health disparities.

Dr. Harris’ involvement in the professional healthcare community spans many leadership positions at state and national organizations. She became the first Black woman elected as president of the American Medical Association in 2020. During her tenure, she focused on a variety of health issues, from opioid addiction to COVID-19. She previously chaired the AMA’s Opioid Task Force, providing evidence-based recommendations to clinicians with the goal of ending the opioid epidemic.

Betty Smith Williams: first Black graduate of the Frances Payne Bolton School of Nursing

Betty Smith Williams was the first Black student to earn a nursing degree from Cleveland’s Frances Payne Bolton School of Nursing, in 1954, and the first Black individual to teach at a higher education institution in the state of California, but her individual accomplishments are only a part of her legacy. Williams has helped ensure that today’s aspiring Black healthcare professionals have the opportunities and support to break down barriers of their own. She was instrumental in developing the National Black Nurses Association and the National Coalition of Ethnic Minority Nurse Associations, Inc. — initiatives that have elevated the voices of Black nurses within the profession. In uniting Black nurses, Williams hoped to create better health outcomes among the Black community. In her own words: "We had no voice, but we understood our culture and our unique needs better than anyone else.”

Join us in delivering our industry-leading pharmacy care to millions of people across the country. As a member of the team, you’ll play an integral role in improving our customers’ quality of life and redefining what’s possible in pharmacy. View our current openings.

Each type of user has a different product or set of products we’ve built for them. From within each product, we collect, transmit, process, and store a tremendous amount of sensitive information. However, our biggest area of security, privacy, and compliance risk is our internal pharmacy management tool called Wunderbar that is used by our operations (ops) users every day to process prescriptions. Securing access to Wunderbar is mission-critical to protect our data and our business, and, of course, we need our super-secure implementation to be super-smooth to avoid slowing down our hard-working ops users.

Developing Robust Authentication Using Rails, Omniauth, and Okta

Alto Pharmacy aims to deliver a better pharmacy experience for everyone who needs medication. To achieve that, we need to enable three different types of users:

Individual customers who need prescriptions

Healthcare providers: the nurses, doctors, physicians assistants, and other medical professionals who prescribe medications

Operations users: the Altoids who intake prescriptions, bill insurance, fill prescriptions, and more

We wanted to be able to change our Wunderbar session lifetimes without hampering either our security efforts or the usability of our product. Moreover, we wanted session lifetimes of other apps to be able to change appropriately with business risk. Before starting this project, we’d implemented a Google OAuth 2.0 authorization flow that allowed ops users to log into Wunderbar via Google and take advantage of transparent session refresh for a limited amount of time.

However, while Google Workspaces was (and is) great for our email, documents, and calendars, it isn’t as configurable or extensible as a proper SSO solution. One painful side effect of this limitation was that, in order to ensure our refresh sessions were limited to twelve hours in Wunderbar, any user of the Alto Gmail drive also had to log back in every twelve hours just to see email — even though there’s not nearly the same level of sensitive data in email.

Plus, our IT team had already picked the tool of the future: Okta. And the goal was to enable SSO, or Single Sign On: if we still used Google for SSO, it wouldn’t really be SSO!

It was clear we needed to move to Okta for authenticating in Wunderbar, too.

Okta is a big company with many different authentication mechanisms. For us, the big question was really: do we want to authenticate via SAML or Open ID Connect (OIDC)? There are a lot of great resources around comparing these two standards and what they’re good at; here’s a good chart comparing and contrasting parts of these two authentication flows:

From this Medium post, which is a great primer on the differences

For us, the most attractive thing about SAML is that it can be used to provision user accounts from your upstream IDP; for example, Okta could be configured to push username, email, group, role, etc., information to our platforms with which we could automatically provision user accounts.

In the end, we decided the OIDC implementation would provide for a very similar user experience to that which our operations users were already accustomed to, with the same capability to perform transparent token refresh.

This transition was pretty easy because we were moving from Google OAuth 2.0 flow to Okta’s OIDC flow. OAuth 2.0 and OIDC are very similar; just know that OAuth 2.0 is technically an authorization framework (once you have a user, what can they access) vs an authentication framework (actually identifying and validating the user). However, there were some odd things about our previous implementation, and I only had one person to blame for those choices: myself. It’s great to get the opportunity to re-implement our authentication system — in a fast moving startup, you rarely get the chance to revisit problems so soon!

The biggest issue at hand with our previous Google flow was the way in which I’d chosen to re-authenticate users whose Wunderbar sessions had expired. In this case, OAuth provides a handy mechanism: a refresh token. Here’s how access tokens and refresh tokens are exchanged from the client and the authentication server in OAuth 2.0 flows:

At the time, we had session lifetimes of 60 minutes when accessing Wunderbar. These cookies also lasted 60 minutes. We faced a problem: if somebody walked away from their laptop for 61 minutes after authenticating, when they came back, how could we make it so they didn’t have to go back through the Google OAuth 2.0-initiated login flow from the beginning?

My solution at the time persisted a secure cookie with the refresh token value client-side with a longer expiration length. Then, if the user didn’t have a valid access token, we’d simply present the refresh token back to the server and get a new access token all over again. This worked well, but exposing secrets to the client always presents a risk of compromise. Refresh tokens are longer-lived, so they're of even higher value to protect!

Okta’s documentation made it very easy to stand up a simple authentication server and set up a local development server. Okta has a great blog post guide with tools we were already using (Rails and Omniauth, specifically) to get up and running. Beyond that, our biggest challenge was ensuring that we had a smooth rollout.

There was an issue in how we’d test and use this flow in our staging environments, however. At the time we were working on this (early 2020), there were two issues:

Our sandbox environment URLs were non-deterministic and could be varied depending upon how an engineer user named their cluster.

Okta apps did not support wildcard redirects in their oauth redirect URLs. This controls where, upon hitting Okta’s servers, they should redirect your payload to handle the meat of authentication.

For a time, our clever infrastructure engineering team managed around these issues with the use of an intermediary keycloak server. However, Okta now supports wildcard redirects that we’re successfully using today:

The biggest functional change to our authentication flow was in our refresh flow. The biggest challenge in landing this change was in how we deployed it to end users in production.

We didn’t want to expose the refresh token because it presented too much risk. What do we do instead? Something a little bit risky, but that we preferred after threat modeling our scenarios. Security engineering is often about making tradeoffs given a number of constraints. Today, our session lifetimes are down to fifteen minutes, and our refresh lifetime for an active session (e.g. somebody making at least one request within this window) is 60 minutes. If somebody comes back after their access token expires, that’s fine; we’ve persisted the encrypted refresh token to the database, and we can use attributes from the expired but still cryptographically valid token in order to look that refresh token up.

This was crucial for Okta especially because Okta refresh tokens are valid for 100 days by default!

Disruptive change is hard. We didn’t want to disrupt the workday of our hard-working ops users who are caring for our many customers and provider partners. The biggest intent here was to keep a safety blanket fallback to the old authentication flow until we were quite confident in its functionality. This broke down into a multi-phase approach:

1. Dark-launch the new Okta flow hidden behind a URL and with a small allow-list of users (mostly just the Security team) assigned to the new application in Okta.

2. Ask for volunteers! These volunteers would go about their normal work day in a variety of functional areas (customer care, pharmacy, fulfillment, engineering) using Okta instead of Google.

3. Change the default login flow to use Okta, but keep Google working just fine as a secondary action hidden behind a URL.

This allowed us to always ensure that we didn’t disrupt peoples’ days too much!

We achieved our goals and now, nearly two years later, we’re successfully using Okta’s OIDC flow within our core pharmacy management app. What did we learn in the process?

Not every API is necessarily fully implemented in every client. At the time of implementation, Okta’s Ruby client wasn’t fully supported. In order to support our refresh flow, we needed to upstream a small change into the client library, which required a little investigation.

Exposing secrets involves risk! In our case there wasn’t a glaring need to expose refresh tokens client-side at all.

Slow rollouts are great, especially with disruptive changes! A big thank-you to our team members who were willing to be part of the experiment group last year when this rolled out.

Interested in learning more about engineering at Alto? Follow us on LinkedIn and check out our open positions.

Face and fingerprint ID login is a convenient, seamless way to gain app access on a mobile device. Instead of typing in a lengthy, hard-to-remember username and password, many apps allow you login with just a quick scan of your face or fingerprint (also known as biometrics).

Considerations and Approaches for Implementing Biometric Login: Part 1

It's a desirable feature for both our end user and the Patients Team here at Alto — we want to make it as easy as possible for users to log in while also performing more frequent authentication checks. Improve the user experience and the security of our app? Sounds like a win-win.

As an engineer, implementing biometric login might seem easy, as mobile devices already capture, manage, and encrypt biometric data and expose APIs for app developers like myself to initiate a biometric scan. All I need to do is call that API and wait to hear if the scan is successful or not. What isn't as simple, though, is figuring out what to actually do with a successful biometric scan response. What does a successful scan mean, and how does that relate to the username and password credentials that users currently use to access our app?

This post walks through the decision points we encountered while implementing biometric login and how our healthcare privacy concerns influenced the final implementation approach.

Prior to implementing biometric login, the only way for users to access the Alto app was with email (username) and password. A valid email and password generates a session, which expires at some frequency. Once the session expires, the user must re-enter their email and password to regain access to the app.

From the beginning, we knew that biometrics would need to be built with our existing email and password session management in mind. This is made clear in the Apple developer docs: "Use biometrics as a supplement to something you’re already doing. Don’t depend on biometrics as your only authentication option."

Make it easier for users to login. Nobody likes typing in an email and password — especially on a mobile app. Our goal was to reduce the number of times a user must enter their email and password.

Enhance the security of our app using more frequent authentication checks. As a healthcare app that displays Personal Health Information (PHI), conducting more frequent authorization checks decreases the likelihood of PHI becoming exposed to an unauthorized third party.

Have the ability to revoke biometric access from a particular user. Similarly, we want to be extra careful to ensure that if a device is lost or stolen, we have a fallback plan to invalidate a user's session and protect the user’s PHI. For email and password initiated sessions, this happens when a user changes their password, as any change in login credentials will invalidate all active sessions for that user. We needed a similar contingency plan for biometric login.

There are several ways to use a mobile device's biometrics to authenticate a user, with varying degrees of security.

No server-side authentication. Simply integrate with the device's biometrics as an extra layer of authentication. If the biometric scan is successful, let the user proceed into the app.

Provides an extra check and gives your app a sense of modern polish

No server-side validation means that nothing is being validated against your system, so this is not a good substitute for account authentication. Therefore, even if you add this check, the user should still be prompted to re-enter their email and password at the same frequency as before.

Given this, this approach wouldn't help us reach our goal of reducing the number of times a user must enter their email and password.

This approach is a good fit if your application already has an existing login and session management system, and you want extra authentication checks throughout the user's session without modifying any other part of the system.

Tie biometrics to our existing email and password authentication. Use the user's biometrics to unlock an encrypted version of their email and password credentials. When a user sets up biometric login, store the user's login credentials within the device's keystore — the keystore will automatically encrypt the credentials. After a successful biometric scan, retrieve those credentials from the keystore and send them to your existing login API.

Still easy to implement, no backend changes needed

Biometric scan can be used in place of entering an email and password

Changing email and password credentials will revoke biometric access: if a user changes their credentials, their biometrics will access stale credentials and fail to login. (This is somewhat of a con as well — it provides a poor user experience, but it's an edge case that should happen infrequently.)

There is still only one way for a user to authenticate server-side, but now two ways to pass server-side authentication — essentially weakening your app's existing account security.

This approach effectively hands out internal login credentials to third party storage. While not a huge risk considering a device's secure storage is encrypted and trusted by most users, it’s not necessarily a best practice either.

This approach is a good fit if your application doesn't contain sensitive data, and your goal is to make it more convenient for a user to login by replacing email and password with a biometric scan.

Create a separate authentication mechanism for biometrics. Introduce a new authentication mechanism specifically for biometrics, resulting in two independent forms of server-side session authentication: email with password and biometrics. The implementation could look like generating a keypair or a shared secret to save and validate against the server whenever a user attempts to login with biometrics.

Biometrics is now tied to its own secure server-side authentication mechanism, which means it can be used independently of email/password (or even replace it, if you choose to).

Two layers of authentication adds security to the app. Not only does a user need a valid email/password session, they also need a valid biometric session.

It provides fine-grain control over a user's biometric session. You can invalidate a user's biometric session by invalidating the public key and can even invalidate a biometric session without impacting an email-and-password session if needed.

Requires building and maintaining a separate authentication mechanism

This approach is a good fit if your application contains sensitive data (e.g. PHI or financial information), and your goals are to make it both more convenient for a user to login by replacing email and password with a biometric scan while also strengthening the security of your account management system.

Because we are a healthcare company dealing with sensitive data, we chose this last path. It required greater engineering investment, but we agreed it was imperative that we maintain a secure system while introducing biometric login for users.

In part 2, we talk implementation details, including the library we used, code snippets, and questions to consider before you get started. Interested in learning more about engineering at Alto? Follow us on LinkedIn.

In honor of National ERG Day, which falls on November 17 every year, we’re highlighting the important work of Alto’s six ERGs. 

Celebrating National ERG Day at Alto

The history of employee resource groups (ERGs) in the U.S. dates back to the 1960s, when a group of Black employees at Xerox self-organized to discuss their experiences of workplace discrimination and advocate for more inclusive policies. At the time, these networks of employees united by a shared identity or experience were known as affinity groups.

Today, ERGs can be found at companies of all sizes and industries where they play an important role in shaping an inclusive culture and fostering a sense of belonging in the workplace. In honor of National ERG Day, which falls on November 17 every year, we’re highlighting the important work of Alto’s six ERGs. 

At Alto, we believe that every perspective matters, and that diversity fosters creativity and leads to innovation. Our six ERGs are part of our broader commitment to diversity, equity, and inclusion (DEI), both in creating our company culture and delivering an exceptional pharmacy experience.

"At Alto, we’re committed to building and sustaining an inclusive workplace that both supports our employees and helps us deliver on our mission to improve the quality of life for everyone who needs medicine,” shared Ty Bledsoe, Head of Diversity, Equity & Inclusion. “Our ERGs help foster authentic relationships, offer safe spaces for education and conversation, and celebrate the incredible diversity of our Altoids and our communities."

By building community, providing support, and contributing to an individual’s personal and professional well-being, these groups help ensure that every Altoid feels a sense of belonging each day at work and that we appreciate the diversity of the customers we serve.

Here are just a few ways that each Alto ERG contributes to a more inclusive culture and pharmacy experience.

Umoja’s mission is to inform, educate, and empower Black Altoids and allies. The group has deepened Altoids’ understanding of the Black experience by sharing educational resources in support of Black History Month, Juneteenth, and Pride.

They also help our team explore the intersection of identity and healthcare as it relates to our services. After Dr. Reverend Stacey Edwards, founder of Fertility for Colored Girls, spoke at Alto about the fertility journeys of Black families this spring, Umoja continued the conversation by inviting Dr. Temeka Zore, OB GYN and reproductive endocrinologist at Spring Fertility, and Esther Ebeuhi, a licensed doula and birth equity analyst, to speak on Black motherhood.

Alto Auténtico aims to build community among Latinx Altoids and ensure that they have a voice at Alto. In addition to facilitating company-wide learning about the Latinx experience and the diversity within Latinx culture, Alto Auténtico’s mentorship program connects junior and senior Latinx team members for coaching sessions and professional development. The group is also working with Alto’s operations, product, and marketing teams to establish a bilingual team to better support Spanish-speaking individuals using our pharmacy services across our communities.

Proud unites LGBTQ+ Altoids and allies in creating an environment where all Altoids can be their most authentic selves. The group has led Alto in celebrating important LGBTQ+ awareness days with events such as drag queen bingo nights for Pride and LGBTQ+ history month. Two Proud members who identify as bisexual gave a talk for Bi Visibility Day on September 23 and also shared their experiences of coming out in in observance of National Coming Out Day on October 11.

Proud also invites experts to speak at Alto about a range of LGBTQ+ issues. They recently hosted a session with Chris Tompkins, author of Raising LGBTQ Allies: A Parent’s Guide to Changing the Message from the Playground, and a fireside chat with Dr. Lisa Capaldini, who has focused on HIV since the beginning of the epidemic.

Women of Alto + Allies (WOAA) helps create an inclusive community for women at Alto with mentorship and networking opportunities that advance their leadership potential. Their newly launched initiative, WOAA Project Spotlight, celebrates female-identifying team members who have helped us deliver on our mission while living our values, and a quarterly webinar series shares how various self-identifying Altoid women launched their careers.

Working Parents + Allies facilitates discussion and collaboration in celebration of our working parents. The ERG has led Alto in supporting working parents with a variety of initiatives, including a community event with the Kids & Art Foundation’s Purvi Shah in honor of Bereaved Parents Month this July; an “Ask a Parent Anything” Slack advice hotline for parents, caretakers, and allies; and free access to Outschool’s live online classes for kids ages 3-18.

And with their second annual Holiday Giveback Program, which donates gifts to kids and families in need through Marine Toys for Tots and the Boys & Girls Club of America, Working Parents + Allies is an example of how our ERGs look for opportunities to give back and show support beyond the immediate Alto community.

Blog

Get to know Jake Moffatt, Engineering Manager on the Alto Assistant Team

Meet the Newest Members of Our Advisory Board

Why We Switched to React Query for Managing Server State

Two Engineering Interns Weigh In: What to Expect From Your Alto Internship

Five Black Healthcare Leaders to Celebrate

Developing Robust Authentication Using Rails, Omniauth, and Okta

Considerations and Approaches for Implementing Biometric Login: Part 1

Celebrating National ERG Day at Alto

Meet Ramiah Martin, VP, Operations & Supply Chain

Celebrating National Coming Out Day at Alto

Introducing Christopher Tidball, Director of Product Management - Supply Chain & Fulfillment

Get to Know Alto Auténtico, our Latinx ERG

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