Tolithia Kornweibel, chief revenue officer at Gusto

Tolithia Kornweibel is the Chief Revenue Officer at Gusto where, previously, she served as Chief Marketing Officer. Prior to Gusto, Tolithia was the VP of Customer Experience at Esurance. Tolithia graduated Phi Beta Kappa with a bachelor’s degree in English from San Francisco State University. She lives in the Pacific Northwest with her husband, Chuck, and their rascally pets.

What’s something you believed early in your career that you now think is wrong?

Earlier in my career, I definitely believed that luck played no part in business success — that success was achieved based on effort and capability.?

I came to understand quickly that work is a reflection of society and has the same systems of disadvantage and privilege. Also, a female Sales leader I look up to named Tessa Prescott, who says, “There’s a lot of luck in sales.”

It’s why I believe that understanding the business model you’re in and seeking sponsorship are so vital — you have to be ready all at once to hustle, deploy developed skills, and mitigate or take advantage of tailwinds or headwinds to succeed.

You transitioned from Chief Marketing Officer to Chief Revenue Officer at Gusto, which is an unconventional move. What motivated this change, and what are the unique challenges you've encountered in your new role?

While my path is relatively unconventional for B2B, it’s relatively common for B2C for larger consumer purchases, and that prepared me well to understand Gusto’s growth motions including inside sales.?

I was motivated to pursue this role because of a compulsion to help more small businesses and entrepreneurs. I believe Gusto allowed me this opportunity because of that—and because of the priorities framework I put in place for all marketing teams I lead:?

1. We are accountable and thus we optimize all the way down the funnel; there is no concept of a “handoff.”?
2. We are accountable and thus we optimize across the customer journey; acquiring customers is the beginning of our work, not the end.?

One unique challenge I faced was my own shaky confidence that I could provide support and counsel to experienced sellers that would be additive. I am blessed with a group of very experienced and expert sales directors who taught and guided me on how to help. And I think my deep understanding of our customers and business model has helped my teams easily parse my thought process and leadership objectives.

Could you share some key insights or strategies from your marketing background that you've found particularly valuable in your current role as Chief Revenue Officer?

The Lifetime Value (LTV)/Customer Acquisition Cost (CAC) sophistication is a real advantage. Understanding not just the math of it, but the levers that drive it, and the modeling possibilities and uncertainties of that calculation gives me the ability to evaluate and optimize our investments across marketing, sales, operations, cross/up-sell, merchandising (pricing, packaging, and promotions) more powerfully than simpler measurements can. Often a background in sales will be less likely to refine your management and decision-making around concepts like sunk cost CAC optimization, marginal investment return, and segment-based LTV/CAC optimization.

I also think that my (ahem, long) background measuring digital and offline marketing investments has trained me to use measurement and analytics more adeptly than folks who have been in operational contexts often relying on industry tools and operational analytics.

This may be spicy, but I also believe fundamentally that if marketers do consider LTV/CAC their responsibility and don’t stop at demand generation or midway in between, they will have a true advantage over many sales teams in being able to see the full value chain from the market through retention and expansion. Often in sales careers, you’re unfortunately subject to the vantage you have once the product has been built, the marketing has been done, and the competitors have positioned themselves, and while you can do a lot from there, your energy is consumed with reactive optimization and upstream influence. Great marketing is throwback marketing: it doesn’t end until the customer churns (and then it focuses on win-back). I look at our teams between marketing, sales, expansion (e.g. cross-sell), retention, pricing as one organism. My job is to help the different systems keep the whole body healthy and thriving.

What do you think is the most significant barrier to female leadership in sales? What advice would you give to women climbing the ladder??

Sales is a career of high earning potential and dynamic, rewarding work. So when I think about diversity within sales, I’m not satisfied with incremental improvement centered solely on gender. We can’t just focus on female leadership as a trickle-down approach to diversity and inclusion within sales. Focusing on intersectionality is a much better strategy. Creating a truly diverse Sales industry means looking through an intersectional lens — expanding the field through race, ethnicity, or national origin as well as gender identity, sexual identity, socioeconomic background, ability, etc.?

My advice to women climbing the ladder starts with women of privilege. Link arms with the folks not invited to the table or appreciated for their talents. The debate on diversity being good for business was settled long ago. Let’s not tip-toe toward a better day.

It’s important for leaders to acknowledge and respond to the realities of inequities, privilege, and homogeneity in Sales. And as problematic as representation is in the industry, inclusion is the thing we focus on the most. While overall I’m incredibly proud to lead a team that’s consistently down for making the industry different, at any time, any of us, can well-intentioned or not, take a misstep or commit a micro-aggression, or miss an opportunity to increase belonging and sponsorship for historically excluded populations of sales professionals.

Don’t mistake me as preaching from a place of arrival. This work is never done. And we’re always on a journey at Gusto to create that better day.?

What are your top tips for making the sales-planning process less painful? What are the biggest pitfalls with planning, and what lessons have you learned over the years?

Top tip 1: Your finance partners are builders with you. Consider how you work with them. You shouldn’t be negotiating. You should be co-creating the future with them. Invest in understanding how they do their work, and educating them on how our teams do our work.?

Top tip 2: Be cautious about the breadth and strength of your opinions on sales planning if you haven’t educated yourself about the overall company financial dynamics, trajectory, levers, and risks. This is a hard one because often the tenure for high-level sales leaders is very short. But the spirit is: while you may be an expert in the veracity of what a great sales motion can accomplish, that never exists in a vacuum.

Top tip 3: Challenge conventional wisdom. At Gusto we’ve disrupted ourselves on concepts of territory planning, quota models and setting, and forecasting. (Another area where marketing, analytics, and operations backgrounds come in handy.) The old school B2B Enterprise model rewards leaders who can align plans to the pipeline, but our jobs should be to accelerate business growth, based on incrementality and optimization. Predictability is valuable to managing shareholders, but our true value to an organization is our ability to grow as smart and fast as we can at all times.

Bonus Q: Who designed the iconic Gusto piggy bank?

Penny was the invention of Jess Chan, a product designer, and very early and very crucial builder of Gusto. Penny pops up while pages are loading—it was created as a solution for replacing customer pain with reassurance, value and peace of mind.