If there were ever a fantasy football league for sales leadership, Stevie Case would be our first draft pick. As Vanta’s CRO, Stevie oversees the company’s go-to-market functions, which comprises about 200 folks globally and has been instrumental in driving transformative initiatives that have propelled the company’s annual recurring revenue (ARR) to $100m. And her creds don’t stop there: before Vanta, Stevie was the VP of Mid-Market Sales at Twilio, joining as one of their first account executives and growing the sales team from a dozen to over 1,000 and generating more than $400m in ARR.

Stevie’s seen it all, from a startup’s pre-revenue journey, where she was the first non-technical hire, to building and scaling go-to-market strategies for unicorn tech companies. 

With all the experience Stevie brings to the table, it’s worth heeding her advice. We were lucky to sit down with Stevie and get super tactical about everything from the transition from founder-led sales to building and scaling a sales team to structuring compensation plans and moving into enterprise sales. 

Here are the key takeaways from the session.

Transitioning from founder-led sales to your first sales rep

Do: Look for a Renaissance Rep.‍

Don’t: Be dazzled by logos on a resume.

Before Twilio, Stevie joined a startup as the 16th employee and first non-technical hire. The scenario was the epitome of founder-led sales: no customer support, no success team and no sales structure in place. With no existing pricing or go-to-market framework, it was a blank slate. 

For founders in this position, the initial mission is to carefully consider who to place in the sales seat. “The most common mistake I see is being dazzled by a great resume,” says Stevie. “You see somebody with a lot of logos and think they know what success looks like.”

The reality is that transitioning from founder-led sales to a sales-driven process requires a different skill set. The sale at this stage looks starkly different, and those with flashy resumes might not know how to navigate it, Stevie says.  

You can avoid this by digging into where their sales opportunities came from in their previous role, Stevie says. “Did they source them themselves? How much of it was inbound? And what was their win rate? You want them to be able to articulate how they succeeded. There are a lot of people who have been along for the ride at a great company and witnessed tremendous success, but they aren’t able to generate that success on their own,” says Stevie.

The ideal candidate for this role is what Stevie calls a "Renaissance Rep".

"They're somebody who's had one or two sales jobs, knows what it's like to hunt and be on quota and can also put the mechanics of deals together. They look more like entrepreneurs than salespeople in many cases."

You're also looking for someone who can help you define your value proposition, provide a starting point for pricing and pinpoint who sees the most value in your product. 

Once you've got that person on board, they need to be shadowing the founders in every customer interaction. "At that point, there's no playbook. The only way to sell is if you're able to speak like the founder," says Stevie.

Stevie has seen founders quickly hit failure mode if they take a step back from sales as soon as their rep joins. "It's risky and ill-advised to think, 'I've hired my salesperson, they can listen to a few calls, attend a few meetings and then suddenly they go off and sell'. Unfortunately, it doesn't work that way. For those first three months, the founder still needs to take 100% of the load in customer and prospect meetings. That time commitment should shift down over the following weeks and months." 

Building and scaling the sales team

Do: Hire 2 people in sales. 

Don’t: Scale until you have repeatability. 

You’ve got your Renaissance Rep and now the journey to scale and build a go-to-market strategy truly begins. But don’t expect things to change overnight, Stevie says. “You want to start small. It’s going to take longer than you would hope or expect. It’s going to take six to nine months for that salesperson to ramp and be truly capable of telling the story in an effective way.”

Hiring one salesperson can be risky as it’s hard to assess their effectiveness. “If you put two people in sales, then you’ve got a comparison point,” recommends Stevie. This dual approach allows you to emulate the traits of the more successful rep.

In the early days, goals are important for those two reps, but Stevie has seen founders get a little too obsessed with imposing industry-standard quotas prematurely, especially if the startup is pre-product market fit. 

Instead, Stevie recommends focusing on controllable actions. “If your goal is to land logos, your sales rep's goal could be to set 20 meetings that month, with at least 25% of those in-person. That’s a great goal they can control and allows you to assess their skills and see if they have the energy and will required.”  

From there, repeatability is key.

“If you throw more people into a go-to-market scenario where there’s no repeatable success, it’s a recipe for failure.”

When you’ve got 80% of your reps consistently hitting 80% of their goals, that’s when you can start to think about scaling, Stevie says. “You want your first two reps to start to feel overloaded. You want them to feel momentum and success.”

In a similar vein, you don't need to add extra sales functions until your core team is overwhelmed. At the start, your reps can handle their own enablement and, in partnership with the founder, be their own sales development representative early on, advises Stevie. From there, it's about optimising outcomes. "You should think about another function when that function can materially move business metrics. I add enablement when I believe enablement can increase a rep's productivity in a way that's positive ROI for the business."  

Identifying and promoting sales reps

Do: Balance internal promotions with external hires. 

Don’t: Promote high-performing lone wolves.

Determining which salespeople are ready for a promotion is a nuanced challenge. Many assume the only upward path is through management, but Stevie emphasises that this is a misconception. “No doubt, some salespeople make great sales managers. But I’m equally a believer in the idea that you can continue to advance in your career without becoming a manager,” she says. 

Those who excel as managers must genuinely enjoy managing people. "The truth is, as a sales manager, you're typically making less money than your top salespeople, and you know it. So you have to have a real passion for wanting to develop people," says Stevie. 

One key indicator of a potential manager is a salesperson who naturally steps up as a team lead, sharing best practices and mentoring peers. This proactive behaviour often signals readiness for a manager role.

Conversely, if their strengths lie elsewhere, forcing them into a role that doesn’t suit their skills can be detrimental to both the individual and the team. “If you have a top sales rep who is crushing their quota, but they’re a lone wolf, do not make that person a manager,” warns Stevie. 

A balanced approach to promotions involves a mix of internal promotions and external hires. "Best practice, from my perspective, is a 50/50 split. If you go too far one way or the other, you either get too insular and focused on how things work today or break the system altogether," says Stevie.  

Structuring sales compensation

Do: 50/50 earnings split between base and variable components.

Don’t: Tie the variable component to more than two metrics.

Stevie is a strong advocate for introducing variable compensation from day one. This ensures that salespeople are motivated by outcomes, aligning their interests with the company’s success. 

However, she cautions against committing to overly detailed compensation plans during the interview process. "That's a red flag," says Stevie.

"You need somebody driven by variable compensations but not seeking certainty around it. They need to be willing to bet on themselves."

As a starting point for your compensation plan, Stevie recommends a 50-50 structure, where 50% of a salesperson's earnings come from a base salary and the remaining 50% from variable components. In the early days, she suggests keeping the compensation period short–monthly or quarterly–tying the variable component to one or two clear metrics. "It could be logos, activity or dollars depending on where you're at. Two metrics work well together if you do dollars, but if it's dollars from a new logo, you get twice as much credit for that versus dollars from an existing logo."

Account managers who focus on existing customers require a different compensation structure. At Vanta, account managers are rewarded based on net retention, which encompasses both customer retention and expansion. "Everybody makes their number in a different way," says Stevie. Some people are stronger on retention, and others are very sales-minded and go heavier on expansion. We wanted to give them the flexibility to play to their strengths."

Consumption-based businesses present unique challenges in structuring sales compensation. “There’s always a huge risk because you could bring in a million dollar customer, but if it’s not committed and they never realise the usage, you could get yourself in a hole where you have to pay your salesperson a huge cheque,” warns Stevie.

Pay commissions based on actual consumption helps mitigate the risk of overpaying for deals that don't materialise. However, this can delay earnings for salespeople, especially if usage ramps over time. To balance this, Stevie suggests incorporating committed contracts that de-risk early payments. "You could combine two metrics: consumption-based payments with a flat amount for new logo sign-ups to provide an immediate reward that also aligns with long-term incentives."

Selling to enterprise companies

Do: Understand the intricacies of the enterprise buyer’s decision-making process and requirements.

Don’t: Underprice your product.

One of the first considerations when selling to enterprises is understanding how these buyer’s process. Unlike small companies, where decision-making might involve one or two individuals, enterprise sales require navigating a maze of stakeholders, Stevie says. This includes the buyer, the champion, procurement, legal and security teams. Each group has its own requirements and concerns, making the sales process significantly more complex. 

The sales cycle for enterprise deals is inherently long. At Vanta, for instance, selling to small companies can take less than a month, while enterprise sales can span six to twelve months or more. This extended timeline must be factored into your revenue projects and sales strategy. "How will you focus your sales reps and what will you ask them to do if it's a long sales cycle? You might want to target them on activity because getting them to set meetings will start to drive that process, whereas if you're selling to smaller companies, a quota may be more appropriate because they can drive dollars fast," says Stevie. 

A frequent mistake Stevie observes is founders underpricing their enterprise product. “Founders have a view that enterprise is price sensitive that isn’t necessarily real. The reality is there’s a mentality in enterprise that if you have a low-priced product, they actually get concerned and think, ‘What’s wrong with this?’”. 

Developing a pricing strategy that aligns with an enterprise buyer's expectations and the sales effort required is crucial. "If you're going to fly around in and be in the boardrooms of all Fortune 500 companies, that's an expensive sales motion and you need to have pricing that makes that economically viable," says Stevie. 

Stevie's experience joining Twilio pre-IPO when it was a completely product-led growth motion highlights the challenges and solutions associated with consumption-based pricing in an enterprise context. "It was all consumption-based and no committed contracts, so the mandate was to build an enterprise business. Enterprises struggle with consumption-based pricing because they need predictability as they get budget pre-approved a year or more in advance. Somebody's job might be on the line if they accidentally send too many text messages and run up a huge bill!".

To address this, Twilio introduced cost control mechanisms, allowing enterprises to set spending thresholds to avoid unexpected costs. Additionally, they created minimum guarantee contracts where enterprises commit to a base level of spending, providing more predictable revenue streams for Twilio. “We’d ask them to commit to a monthly minimum guarantee for 12 months minimum. A committed recurring contract is good for business because it’s ARR and not wild consumption that’s going up and down,” advises Stevie. 

Twilio evolved its model to include subscription-based products alongside consumption pricing to further align with enterprise needs. This hybrid approach offered a flat fee for a bundle of enterprise features, ensuring a baseline of predictable revenue while still allowing for consumption-based flexibility. 

Key takeaways

• Hire a Renaissance Rep for early-stage sales. Avoid being dazzled by big-name logos on resumes; focus on candidates who have proven they can generate success on their own. 
• Shadowing and integration for new sales hires. Ensure your first sales hire/s closely shadow the founders in customer interactions for at least the first three months. 
• Start small and compare performance. Hire two sales reps initially to allow for performance comparison. Set controllable, activity-based goals to assess their effectiveness first before implementing industry-standard quotas. 
• Take a balanced approach to sales compensation structure. Implements a 50/50 split between base salary and variable components tied to clear, achievable metrics. 
• Think through your enterprise sales strategy. Understand the intricate decision-making process of enterprise buyers and ensure your approach to pricing is aligned with their needs and reflects the value and effort required to secure these deals. 

About Vanta

Vanta is the leading trust management platform that helps simplify and centralise security for organisations of all sizes. Vanta has over 450 customers in Australia and New Zealand, including Atlassian, Dovetail, OFX, Joyous, Constantinople and Askable. The Airtree community can access $1,000 off Vanta here.