CXO career trajectory in Tech, With Lexi Reese – CB50

General Overview

Lexi Reese currently works at Gusto, which works with businesses of all sizes on process issues like payroll, onboarding, etc. Previously, she was at Google and American Express. She also has a MBA from Harvard Business School. Because she’s worked on both the operations side of a business and the customer experience side — and usually at large companies — I wanted her perspective on career trajectories. That’s the focus here, although we touch on a number of issues.

About Lexi

Jeanne Bliss Lexi ReeseOne of the top female executives in Silicon Valley, Lexi strives to empower women and other underrepresented groups at Gusto and create a vibrant and inclusive workplace culture. She also ensures that Gusto is continuously going above and beyond to serve all customers.
Lexi’s passion lies with helping small and medium business owners succeed. This interest was sparked by her early career in microfinance as a public policy advocate with ACCION International,  giving loans to people living in poverty to start their own ventures.
She later worked at Google for eight years, most recently serving as Vice President of Programmatic Sales and Strategy globally. Lexi also started the Cambridge AdWords team for Google’s small business organization. These experiences inspired her to continue supporting small business owners, whose success positively impacts their families, communities, as well as local and national economies.
Lexi has an MBA from Harvard Business School and graduated Phi Beta Kappa with a bachelor’s degree from the University of Virginia. She lives in the Bay
Area with her husband and two daughters. She was mentioned in this Vogue article on women in tech not too long ago.

“Head, heart, and gut”

Lexi says the best advice she ever got was to make career decisions from a mix of those three places. Her true passion is small business, as you can see even with her Google work — she launched the Cambridge (MA) AdWords team, and AdWords largely benefits small businesses. (It levels the playing field.) Gusto is a solution marketed to small businesses. This is all logical: Lexi’s family was a series of small business owners.

The necessary skills for this work

“Nothing trumps passion,” she admits, but also notes these three for building a business or scaled technology organization:

  • Ability to drive the business: Establish a purpose, set priorities, drive objectives, explain what results will look like, and communicate.
  • Team-building: You need a place where people feel OK being authentic. Gusto’s founders are all immigrants (1st/2nd generation) and their connection to the work is thus very raw and real.
  • Be self-aware: This is a big one. Take the time to understand how you show up as a leader. Have a growth mindset. Self-reflection is not at a premium in most offices, but it needs to be. One aspect of this is also developing resilience and knowing when you’re about to burn out on something. See your friends. Take a break. It’s OK.

One note on SaaS models 

One of Gusto’s founders is now Head of Product. Before Lexi got there, he also led customer experience. Why? Recall what SaaS means: software as a service. By definition, the customer experience is the product. In those models, the founder 100% has to understand this and not view customers as costs. Unfortunately, many still do — even in SaaS!

The Extra Mile

This is a great program from Gusto. The CEO of the company is currently on a cross-country road trip rewarding some of their best small business partners and fully tying together the customer experience element of what Gusto does. In this episode, Lexi talks about Paws and Stripes in Albuquerque.

Book rec and early steps

One of Lexi’s favorite books is Uncommon Service by Francis Frei. She views Frei as something of a mentor, and decided to begin her time at Gusto by going and talking to customers — and those who were customer-facing.

She found out some things she had expected to find out — such as Gusto saves headaches at payroll time, which is how they market themselves. But she also found out interesting new things. For example, in Gusto an employee has access to their own payroll records. At big companies that’s not normative, but it’s huge for small businesses when they don’t have a dedicated HR or payroll person. They can use the employee to screen their own information, and that saves them time and hassle. At the time, that hadn’t been a huge value prop for Gusto, but it emerged as more and more of one with customer interviews.

How to get from 15,000 customers to 100,000 customers

This is all about repeatable, scaleable process. First the executive team needed to be aligned and there needed to be some alignment re: the work.

First up: define the customer journey. Analyze different customer segments, map out the journey that specific customer goes through. This involved discussions with Engineering and Product. There are issues with payroll transfer — when someone comes on-board with Gusto, they usually have to pipe over their payroll info from another payroll company. What happens when the state government sends them a flag or issue because of errors with the piping over? All these concepts needed to be tested to understand the good/bad of customer experience.

Second up: put the journey together. This is experience + data + conversations. Where are you not as good? Those areas will get more exposed at 100,000 customers. Focus on ways to minimize those issues.

Third up: tie this to employee experience. This involves customer survey results, training, and interactions between leadership and employees.


This is a way to balance fast growth with a high level of service. (A challenge throughout tech.) Customer advocates and leadership come together for days and deal with support issues, the queue, etc. It also frees up some engineer time, which is a vital resource in tech companies. Previously, companies dealt with this issue by hiring more people to call down a support queue. But Lexi felt that a backlog of customers waiting for support was actually a leadership issue, not necessarily a customer service/experience issue.

The Help-A-Thons help get customer loyalty and happiness back on track quickly. If you just hire people to call down a list, you may not get that reaction.

“The reactive mode” and “panic time”

Avoid this. That’s what happens when you hire people to solve the problem above. You’re just reacting — not responding. (It’s the same problem many people have with email, especially on your phone.) Reaction is good in some situations, but it kills long-term decision-making and productivity.

Roles will expand, especially with tech

Lexi’s role expanded in ’17. She took on some sales and marketing operational ownership. She has good answers on this topic in the podcast, but one of the best bottom-line answers is this: if you are growing 10x every year, roles are naturally going to change. The depth and breadth has to shift. There’s no way around that, especially in a high-growth context — as many companies are, either within the tech industry or because of the tech industry.

“Pay It Forward” question

What do you know NOW that you wish you knew THEN? Lexi notes:

  • Be OK with being bad in the service of being great: Not everyone is perfect. Avoid the generalized average. Listen to your customers, via tech and in person. Be excellent for them. Don’t be afraid if a set of person you’re not designed for doesn’t like your service. Don’t penalize your customer-facing people when that happens.
  • Always listen to the customer: This should never stop. If you haven’t talked to a customer in two weeks, it’s hard to consider yourself a leader. Get on the phone.
  • Hire for “stunning” and “diverse:” If you’re trying to serve the world, it can’t just be people from the town your HQ is in.
  • Engineer solutions with the customer in mind: If you get a question 10 times from a customer, never get it an 11th time. The product should be fixed or the content library should be updated.

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