Stevie Case on Building Sales Teams, Moving Upmarket and Leading With Empathy

Stevie Case, Vanta's chief revenue officer, tells Harry Stebbings that her career began far from sales. She was studying at the University of Kansas with plans for law school when gaming took over. In the late 1990s, she became what she describes as the world's first female professional gamer.

Living in a gaming house introduced Case to technology and computers; she learned to build her own PC to compete. She later made games in Dallas and mobile games at Warner Bros. A vendor, Matt Golden of Terra Wireless, offered to teach the shy product manager to sell. She accepted because it sounded challenging, and learned by accompanying him on the road.

Case says she remains an introvert. Golden taught her that showing genuine vulnerability can make other people comfortable opening up. In her view, a salesperson can be knowledgeable and confident about a product while also acknowledging that they are an imperfect human being.

Her gaming and product background still shapes her work. Early game teams had to understand software, marketing and distribution, often without the benefit of social virality. That experience gives her empathy for the people building software today.

Games also require strategy, adaptation and math. Case sees the CRO's job similarly: combine different elements into a strategy, constantly adjust, and measure the outcome in revenue or users.

A single mother with full custody since her daughter was three, Case recalls taking sales calls while driving to daycare and school. Early on, the responsibility made her hungry to succeed and provide for her daughter; later, she says, it made her more conscious of the time work took away from her family.

Case describes stubbornness, desperation and a desire to prove doubters wrong as early sources of motivation. She had to ask herself why she could not have both a family and a career, and decided to do everything she could to make that possible.

She believes assumptions that parents are less committed still exist, although she has seen more workplaces where people can be both caregivers and successful professionals. Her advice is not to apologize for having a family or accept someone else's account of what it must cost your career.

For leaders trying to create an inclusive environment, Case starts with genuine interest in the lives of employees. People want to be seen as whole human beings, she says; a manager need not have lived the same experience to listen and make room for it.

At Twilio, Case joined as an enterprise seller shortly before the IPO. George Hu arrived later and, she says, helped make the case for sales and go-to-market. He became a mentor and sponsor who challenged her to find her own way into important conversations rather than simply opening every door for her.

Hu also taught Case to think about the operating model behind revenue. She recalls Twilio discussing a move from a roughly $200 million run rate toward $1 billion, but says the ambition needed a concrete model: the mechanics and assumptions that could make growth more predictable rather than a matter of hope.

Can a startup run product-led growth and enterprise sales from day one? Case says it depends, but cautions that combining both too early can confuse customers and create disputes over which salesperson gets credit for a self-service signup that later becomes a deal.

For a company starting with product-led growth, she would focus first on customer enablement and success. Sales can be added experimentally: put a person into a customer relationship and see whether that creates more revenue while also solving a problem the customer values.

The ideal customer profile matters. Self-service may suit smaller businesses that want simplicity, whereas enterprises can have needs that cannot be fully automated. Case favors product-led growth in enterprise too, backed by salespeople who can address those needs.

Vanta's move upmarket illustrates why the value story changes even when the underlying product does not. Case says smaller customers often want to complete their first SOC 2 process, while larger organizations may want a consolidated view of compliance, time savings and lower risk. She is describing the proposition of the company she leads.

Case says Vanta was pulled toward larger customers by inbound demand while retaining its focus on small businesses. She formed a separate team to pursue midmarket and enterprise opportunities, gave it a different compensation plan and time to experiment, and treated the move as a test.

The experiment was gradual in market scope but not in staffing: the selected people spent all their time on the new segment. Asking the same rep to handle high-velocity small deals and strategic deals, she argues, encourages them to default to the work they know and the compensation they can see.

A founder must create the early sales story: the vision, the customer's problem and why the product matters. Early buyers are placing trust in the founder. A detailed playbook of repeatable steps comes later, once there is enough evidence about product-market fit, the ideal customer and the value drivers.

The first sales hire depends on whom the startup sells to. For enterprise, Case suggests one or two creative sellers who can open doors; for small businesses, a player-coach who understands speed and scale may be more useful. In either case, the founder must remain involved as the business changes.

A prestigious résumé is no substitute for that involvement. Case says the first seller should be close to the founder, joining calls and hearing the story repeatedly, including in conversations with investors and partners. A written document alone cannot convey the founder's conviction or give the seller the context to speak fluently.

Asked to choose between domain experience and experience selling at a particular annual contract value, Case favors the latter: a seller can often learn the subject, but must understand the mechanics of a deal of that size. More important in an early hire, she says, is the ability to hunt for opportunities rather than wait for orders.

Order-taking can be valuable in a well-defined, high-velocity process. In the economic environment discussed in early 2023, however, Case expects grit and the ability to open doors to matter more across sales teams. That is her forecast for the following 18 months, not a guarantee.

Case defines grit as staying with a difficult goal over time and overcoming adversity. She asks candidates about accomplishments they are proud of, including education, hobbies or personal challenges, and listens for evidence of sustained effort and resilience.

She gives her own degree as an example. After leaving university to play games professionally, she encountered employers that would not interview her without a degree. Over about 25 years she took classes intermittently, including at night as a single mother, and completed her undergraduate degree during the pandemic. She did it, she says, to prove it to herself.

For sales hiring, Case recommends several perspectives, including interviewers outside sales, alongside checks for functional competence. She dedicates an interview to grit and uses a role-play or case study to assess curiosity and discovery.

Good discovery is dynamic, she says: ask questions, listen and follow the important clues rather than mechanically checking off a framework. In a long conversation a prospect may reveal one decisive concern. The seller's job is to understand why it matters, quantify it where possible and connect the deal to that need.

Early sales hires must be comfortable with uncertainty. Case cautions founders against being dazzled by big-company credentials and extensive demands for guaranteed compensation. A startup compensation plan should make clear what the seller should spend time doing, and founders should refine it with the seller as the business changes.

In a difficult market, sales leaders should be honest about uncertainty instead of promising outcomes they cannot know. They can also recognize progress earlier in the funnel when teams are missing revenue targets, giving people achievable wins tied to activities that matter.

Case explains that a spiff is a temporary special incentive outside the regular compensation plan. It can reward an activity, not just revenue. She likes cash and recognition, such as a dinner with the CEO, and says the competition should also be enjoyable.

At Twilio, she ran a 'pipe week' to encourage outbound pipeline generation. Team members earned points for activities such as outreach and creating new CRM contacts; the top scorers received cash and other prizes. Her example describes an internal program, not a measured causal result.

Long enterprise sales cycles make new hires hard to evaluate from closed revenue alone. Case says an experienced founder or manager must stay close enough to inspect deals and assess whether they are really progressing. A rep's optimistic forecast can mask the fact that a buyer has gone quiet.

When deals repeatedly slip into the next quarter, Case often traces the problem back to discovery: the seller may not understand the buyer's priorities, timing or internal decision process. A credible close plan requires those details, not just friendly signals from a champion.

She is not opposed to discounting, but warns against making it the only way to create urgency. At Twilio, she recalls bundling enterprise features for an airline at an initially invented $15,000 monthly price, then offering roughly 15% off to close by December 31. Terms, pricing and the cost of delay can all be levers, she says.

In a more constrained buying environment, Case advises bringing the CFO, security leader and other potential decision-makers into the conversation early. A seller who avoids objections and relies only on a champion risks a late surprise; involving stakeholders sooner gives the champion a better chance to resolve concerns.

At Vanta, Case says the sales team discusses value throughout the customer relationship. Historically it emphasized growth, including the possibility that compliance could help customers enter markets or close deals. In the environment at the time of the interview, she expected to emphasize cost savings, efficiency and risk reduction more heavily.

In the quick-fire round, Case says the enduring principle of sales is that people buy from people and want authentic value. By contrast, she thinks high-volume, generic cold outreach has become less effective and needs more personalization.

Her immediate CRO challenge is planning resources amid fast-changing conditions. She cannot know whether the coming period will bring a mild or severe recession, yet must prepare an annual plan. Her rule is to plan for worse and be ready for better.

Case also recalls suing her Kansas school district after it banned a book with a homosexual theme. She says a federal appeals court agreed with her, the book was restored and legal fees were paid. She advises a new sales leader to ask questions freely and seek time with executives.

She would like sales to become more human and empathetic: kindness and strong performance, she argues, can coexist. As an example of a sales experience she admired, she names Clari, a product she had recently purchased for her company.

Case says the Clari representative engaged thoughtfully with her as a person, showed value before the sale and offered terms that persuaded the company to buy despite a budget freeze. The example is her account of a purchase, including the effect of the offer, rather than independent proof of the product's value. Stebbings closes by thanking her for the conversation.