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Leaders in Lending | Ep. 52

Cultivating Operations and Culture in a Digital-First Environment with Anna Counselman

On this week’s episode, get an inside look into how Upstart’s Co-founder and Head of People and Operations, Anna Counselman has helped shape the unique operations side of business and fostered company culture in a remote environment. 

Anna Counselman-modified


Anna Counselman

Anna Counselman is Co-Founder and Head of People and Operations at Upstart. Anna co-founded Upstart in 2012, after a career at Google leading operations. She helped scale Upstart from zero to 200+ employees and originate more than $6B in loans. At Google, Anna led Gmail Consumer Operations for 5 years as it scaled from 150 million to 450 million users and launched the global Enterprise Customer Programs team. She also held a variety of operations roles at McMaster Carr and several other startups. Anna graduated Summa Cum Laude from Boston University with a BA in Finance and Entrepreneurship. Anna received a White House Champion of Change award and was recognized as one of Silicon Valley Business Journal's 40 under 40.



Upstart is a leading AI lending platform provider that partners with banks and credit unions to help them grow their memberships and expand access to affordable credit. By leveraging Upstart’s all-digital, AI lending platform, Upstart-powered lenders can grow consumer loan portfolios, lend to more creditworthy borrowers safely, and deliver a modern, all-digital experience for their members that allows them to originate loans in minutes. Over 70% of loans funded are fully automated with no human interaction.[1]

Key Topics Covered

  1. Anna’s journey from Google to Upstart
  2. The necessity of understanding the consumer narrative to create a powerful back-end experience
  3. Upstart’s digital-first approach to hybrid work
  4. Key lessons learned from Google


Upstart’s culture and operations approach is part of what makes the company a haven for top talent.

However, getting to that point was no simple task.

On this week’s episode, get an inside look into how Upstart’s Co-founder and Head of People & Operations, Anna Counselman has helped shape the unique operations side of business and fostered company culture in a remote environment. 

You’ll learn about…

  • Anna’s journey from Google to Upstart
  • The necessity of understanding the consumer narrative to create a powerful back-end experience
  • Upstart’s digital-first approach to hybrid work
  • Key lessons learned from Google

Product Operations

During her time at Google, Counselman was responsible for helping scale Gmail from 150 to 450 million users with an operations team of only twelve.

Early on, she learned that optimizing an efficient experience requires so much more than stellar customer service—it requires understanding the customer roadmap and pain points in order to troubleshoot with the engineering and product teams.

According to Counselman, the ethos of operations has evolved to the point where, “there should be no customer service because all customer issues can and should be fixed in the product. That’s the starting point.”

Loan document verification

With that ethos as the backbone of Upstart’s operations team, the team has been able to successfully automate and scale back-end processes like loan document verification.

In Upstart’s early days, Counselman and the team would have to verify every document a customer submitted—an already labor-intensive practice that becomes even more meticulous with the use of alternative data sets.

After numerous trials and errors, Counselman’s team drastically started to improve the customer experience over time.

When they discovered that for every additional document they asked for, the customer drop off rate increased 15 percent, they really began to change their processes.

With a first principles-forward mentality, they began reconstructing a new customer journey that wouldn’t require the user to provide additional information—everything would be supplied and verified on the back end. 

After a couple of years of integrating with a variety of third-party services and building multiple machine learning models to predict risk around verification, the operations team was able to automate 70 percent of loan originations.

Human Story & Data

“What I learned at Google is, it's not even just about the data. It's about getting product engineering and ML to care about the problem and the user,” explained Counselman.

With stronger capability and access to detailed data, the machine learning team was able to thread together more holistic consumer narratives with which to apply to their algorithms.

Counselman has since made it a habit of measuring everything possible in a product, both on the operations and product side. 

Spending time and investing resources in understanding the ultimate problem and precise metric to influence is the team’s top priority. 

While systems are set up for those endeavors, Counselman claimed that the magic is in building, “an analytically minded, business savvy operations team to drive the conversation,” and intersecting product engineering, machine learning and operations.


Culture is an invaluable part of the Upstart experience. Counselman gives an inside look into the company’s new digital-first experience and how culture will be fostered in the years to come.

Hybrid work

The digital first approach is inspired by the concept that Upstart employees should be able to live and work anywhere in the United States.

However, in-person collaboration is still central to the company mission.

Counselman and her team developed a strategy where they would pay for all of the expenses to collect teams once a month to meet and collaborate at one of the three offices. 

The intent of the approach was to maximize the flexibility their employees now desired while preserving the magic of building face-to-face relationships, problem solving and experiencing serendipitous moments together.

“Our hope is this allows us to recruit the best talent from anywhere and the best talent is going to have a choice,” she said.

With just a couple of days in the office done efficiently, any remote team can access the invaluable office experience.


Even though the digital-first approach is still in its early stages, the beauty of a startup environment is that iteration is quick and encouraged.

Despite its growth, Upstart still possesses agility and speed in experimentation.

Since a majority of the time employees will be working from home, it’s crucial to create digital spaces that host “water cooler talk” so as to deepen personal relationships and accelerate trust and collaboration.

According to Counselman, Google collaboration tools, Zoom, and Slack have successfully compensated as casual chat room settings.

Upstart’s strong company culture and its implementation in a digital environment is evident in its employee growth.

Before the pandemic, only 400 people constituted all of Upstart. Now that there are more than 1,500 employees who haven’t worked together in an office, and culture engagement measurements have increased, it proves how unified the community has grown even on a digital front.

“The biggest thing I point to is our values,” said Counselman, “I know it sounds so trite, but I made everybody sit in a room and talk about who we are, and who are we not? Who are we the right fit for? And who are we not?”

To this day, the core value set remains the same which has been foundational in attracting the right kinds of people.

Since every second counts, Upstart looks for people who thrive in fast paced environments, want to make an impact and crave growth. 

This also requires equal transparency from the executive board about the state of the company and where it’s headed. Weekly meetings are held to present launches and host Q&A sessions with the founders to keep every employee well-connected to the mission, excited about problem-solving together and moving unified toward a similar vision.

Stay tuned for new episodes every week on the Leaders in Lending Podcast.


Stay tuned for new episodes every week on the Leaders in Lending Podcast