20Sales Why You Should Not Do PLG and Enterprise Sales at the Same Time How To Move Into Enterprise Sales Gradually How To Make a Comp Plan For Sales Teams Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

In a dynamic conversation on "20 Sales," host and sales expert delves into the principles of building successful sales teams with Stevie Case, CRO at Vanta. Stevie, a former professional female gamer and seasoned sales leader, shares her unconventional journey into sales, emphasizing the importance of grit, curiosity, and human connection in the sales process. She reflects on the challenges of being a single mother and a sales professional, advocating for not apologizing for one's life circumstances. The discussion covers the nuances of early sales hires, the significance of discovery in sales cycles, and the strategic use of incentives like SPIFFs to drive sales activities. Stevie also addresses adapting sales strategies to economic shifts, focusing on value-based selling and the need for authenticity and empathy in sales interactions.

• Early hires should have a "hunter" mentality rather than being accustomed to taking orders.
• The grit to open doors and hunt is essential for success in various scenarios.
• A "hunter" is someone proactive and determined, with the drive to seek out new opportunities.

"The most important in early hires. Is that person a hunter, or are they used to taking orders? That grit that it takes to be somebody who can open doors and hunt. That person will succeed over others in every possible scenario."

This quote highlights the value of having a proactive, self-starting approach in early team members, emphasizing that this trait is a strong predictor of success across different situations.

• Stevie Case is recognized as the first professional female gamer and an established sales leader.
• As the CRO at Vanta, she leads the Go-to-market team to support rapid company growth.
• Stevie played a significant role in Twilio's sales team expansion and enterprise business development.
• She is also a founding operator at Coalition Network and an active angel investor.

"And we're joined by a total rockstar in this episode. Not only was our guest the first professional female gamer ever, but also an OG sales leader."

This quote introduces Stevie Case, highlighting her unique background as a pioneer in professional gaming and her expertise in sales leadership.

• Stevie Case did not originally plan for a career in sales; she envisioned going to law school.
• Her interest in gaming led her to the technology and computing field.
• She learned to build PCs to stay competitive in gaming.
• A vendor recognized her potential and offered her a junior sales position, marking the start of her sales career.

"I had no idea what that meant. I was very socially awkward. I thought, this sounds deeply uncomfortable and I love a challenge. Let's go for it."

Stevie Case reflects on her unexpected entry into sales, despite being socially awkward, and her willingness to embrace the challenge, demonstrating her adaptability and growth mindset.

• Stevie Case has embraced her introverted nature and uses it as a strength.
• She learned from a mentor that showing vulnerability can help build rapport with others.
• Stevie believes in being both competent and authentically human in sales interactions.

"The best way to open people up is to give them comfort with your own vulnerability."

This quote explains how showing one's vulnerability can create a comfortable environment for others, which is a valuable tactic in building relationships and trust in sales.

• Stevie Case has been a single mother throughout most of her sales career.
• Parenthood made her more driven and hungry for success, especially in the early stages of her career.
• She balances her professional life with being present for her daughter, ensuring she values her time effectively.

"It's really changed over time, and this is a very fundamental part of my life."

Stevie Case discusses how being a single mother has influenced her career over time, shaping her drive and approach to work-life balance.

• There is still a perception that women may be less reliable post-childbirth.
• Stevie advises women not to apologize for their lives and to embrace their narratives.
• She believes in creating inclusive environments where people can be themselves.

"Don't accept this narrative that it's a balance or a trade off, or you're giving something up somehow."

Stevie Case encourages women not to internalize the narrative that having children is a compromise to their career, advocating for self-definition and honesty about personal circumstances.

• Leaders should show genuine care for their team members and their lives.
• Inclusivity comes from recognizing and accepting the full spectrum of employees' experiences.
• Understanding and empathy from leadership can foster a supportive workplace culture.

"If you show a genuine and ongoing interest in the human beings on your team, that acceptance and that inclusive environment ultimately will be created."

This quote suggests that leaders who take a sincere interest in their team members' lives can create an inclusive work environment that accommodates various personal situations, such as parenthood.

• Combining PLG (Product-Led Growth) and traditional sales from the start can create confusion.
• Focus should be on customer enablement and success rather than immediate commercialization.
• Introducing both PLG and sales motions too early can complicate credit attribution and compensation.
• Early sales require clarity on value proposition and customer experience.

"You can, but I would caution you against trying to do both right away. Think in the early days of sales you have to be very clear on what is the value prop for the customer and what is that experience."

This quote emphasizes the importance of having a clear value proposition and customer experience before attempting to combine PLG and traditional sales strategies.

• Transition to traditional enterprise sales should be tested iteratively, similar to software development.
• The right time depends on whether a salesperson can increase revenue and customer satisfaction.
• The target customer profile influences the sales strategy; SMBs may prefer PLG, while enterprises might need sales support.

"I am a big fan of testing. Sales should be approached in an iterative way that is similar to software development."

The speaker advocates for an experimental approach to sales, suggesting that traditional sales should be integrated when it demonstrates clear benefits.

• Transitioning sales from SMB to enterprise requires a shift in the value proposition narrative.
• The product may remain the same, but the problems it solves and the success metrics can differ between SMBs and enterprises.
• SMBs might focus on compliance achievements, while enterprises might prioritize efficiency and risk reduction.

"The underlying product is the same. We're an automated compliance platform, but our SMB customers are solving the problem of addressing compliance for the first time... our enterprise and mid market customers are solving something very different."

This quote highlights the need to adapt the storytelling around a product to fit the distinct needs of SMBs versus enterprise customers.

• The decision to target enterprise customers should be based on observed success within that segment.
• Creating a dedicated team to focus on mid-market and enterprise opportunities can help validate the potential for growth.
• Testing the enterprise market should be deliberate, with dedicated resources and clear differentiation from SMB strategies.

"We are seeing success that we didn't pursue but came to us in those segments. This is another opportunity for us to start to experiment."

The speaker explains that moving into the enterprise market was a strategic decision based on unexpected successes, which led to a more focused approach to capturing this new customer segment.

• The structure of the sales team depends on the target market; enterprise sales require a few skilled salespeople, while SMBs need a scalable approach.
• The founder should remain engaged during the early stages of building a sales team.
• Hiring based on brand-name resumes without considering the unique needs of a startup can lead to failure.

"You can test it with the caveat that these things are radically different. The way that I'm testing that in our business was to inch up market."

The speaker suggests that testing the enterprise market can be done incrementally, focusing on a specific customer size and learning from successes before fully committing.

• Founders should develop the early sales playbook, focusing on the company's story and value proposition.
• A sales leader can later document the mechanical steps for new reps to succeed.
• The founder's engagement in storytelling and trust-building is critical for early sales success.

"That founder has to be storyteller in chief, because there's an element in early sales of trust."

The quote underscores the founder's role in conveying the company's vision and building trust with early customers.

• The first sales hire should work closely with the founder to absorb the company's vision and storytelling.
• This close collaboration ensures the salesperson can represent the company as if they were a co-founder.
• The founder's involvement goes beyond sales calls and includes investor and partner discussions.

"The single most important thing in that is that that first sales hire has to be glued at the hip. With the founder."

The importance of a symbiotic relationship between the founder and the first sales hire is highlighted, ensuring the salesperson fully understands and can convey the company's mission.

• Understanding the mechanics of deals within a certain ACV (Average Contract Value) range is more important than domain expertise.
• The key trait for early hires is the ability to be a hunter, not just order takers.
• In the current economic climate, grit and proactive selling are crucial for all team members.

"It's actually much more important that somebody understand the profile and they understand the mechanics of doing a deal of that size."

This quote explains that the practical skills associated with managing deals of a specific size are more critical than having domain expertise when making early sales hires.

• Grit involves perseverance in difficult tasks over a long-term period, not just short-term hustle.
• Looking for candidates with a history of sticking to challenging goals through adversity.
• Grit is an indicator of resilience and adaptability in dynamic work environments.

"Grit is about hanging with something hard over a longer term and actually making it happen."

Grit is defined as the capacity to commit to and follow through with difficult tasks over an extended period, which is a desirable trait in a sales hire.

• Explore candidates' proud accomplishments outside of work to gauge grit.
• Early-career individuals can demonstrate grit through education or personal challenges.
• Passion and stories of overcoming adversity are signs of grit.

"You've got to get to the heart of what are some of those accomplishments that person is very proud of and they don't have to be at work."

This quote emphasizes the importance of understanding a candidate's personal achievements and challenges to assess their level of grit.

• Discipline often requires sacrifices, such as missing social events for study or training.
• Pain resulting from disciplined actions is a valuable trait in a sales context.

"I always want to see discipline. That means sacrifice."

Discipline is highlighted as a crucial trait for sales hires, as it involves making sacrifices for greater achievements, a quality valuable in sales roles.

• Personal challenges, such as completing education while managing life's obstacles, are indicative of determination.
• Determination can be more telling than traditional qualifications like degrees.

"I actually graduated and got my undergrad degree during the pandemic. That is the kind of stuff I'm looking for in people I hire, is just the determination."

The speaker reflects on their own experience of determination by completing their degree amidst personal challenges, using it as an example of what they seek in hires.

• Achievements can be driven by personal challenges, not just career advancement.
• Proving oneself capable of overcoming obstacles can be a strong personal motivator.

"I wanted to prove that I could overcome this thing. It wasn't about proving it to somebody else. It was about proving it to myself."

The quote reveals the speaker's internal motivation for completing their degree, emphasizing the importance of personal goals and self-validation.

• Multiple interviews from different perspectives are crucial.
• Involving non-salespeople in the process provides diverse insights.
• Dedicated interviews to assess traits like grit and curiosity are necessary.
• Role-playing and case studies can be effective in evaluating a candidate's skills in discovery.

"You've got to have a full interview dedicated to testing for grit and hearing those stories."

This quote underscores the importance of having a specialized part of the interview process focused on assessing the candidate's grit.

• Curiosity is fundamental to learning and adapting in sales.
• It is essential for successful discovery and closing deals.
• Good discovery is rooted in genuine curiosity and active listening.

"Good discovery is really about curiosity and listening, allowing the person you're asking questions of time to speak."

The speaker emphasizes that effective discovery in sales is based on true curiosity and the ability to listen well to potential clients.

• The 'nugget' is the key piece of information that ties a deal together.
• Salespeople must listen deeply to identify the client's core needs or problems.
• Understanding the 'why' behind a client's engagement is crucial for success.

"You got to be able to listen and iterate and get to the heart of what do they really care about? What are they trying to do?"

This quote stresses the need for salespeople to be adept at discerning the critical information that will help close a deal.

• Early hires should be open to risk and not overly reliant on guarantees.
• Compensation plans should be clear and align with company incentives.
• Willingness to iterate on compensation plans is necessary.

"At the end of the day, what you want out of a great comp plan, early days as a founder, something that is so clear that if a salesperson reads it, they understand exactly what they should spend their time doing when you're not in front of them."

The speaker outlines the importance of having a transparent and straightforward compensation plan that guides sales team behavior.

• Honesty and transparency about the business environment are key.
• Aligning the team with the company's mission builds trust.
• Tactical measures like spiffs can help maintain motivation.

"You've got to find ways to identify the wins that underlie the big numbers."

The quote highlights the strategy of focusing on smaller, achievable goals to maintain sales team morale during challenging times.

• Spiffs are special incentives outside the regular compensation plan.
• They can be tied to specific goals or activities to drive desired outcomes.
• Spiffs are often used for short-term goals or to address specific business needs.

"A spiff is going to work best when you tie it to something else. That might not be directly tied into how they're incentivized in the comp plan, but it's something you need them to do and is important to the business."

The speaker explains that spiffs are most effective when they incentivize activities that are crucial to the business but not directly related to revenue, as per the regular compensation plan.

• Gamification can increase engagement and effectiveness in sales.
• Points are awarded for specific sales activities, such as outbounding and creating new contacts in CRM.
• Weekly score sheets are submitted, with top performers receiving cash and other fun prizes.

"Gents, you get points for a certain kind of outbounding. You'd get points for creating new contacts in CRM. And it was all these activities that lead to opportunity."

This quote explains the implementation of a points system for sales activities, incentivizing behaviors that lead to potential sales opportunities.

• Long sales cycles in enterprise sales make it challenging to measure new hire effectiveness.
• Engagement with an experienced individual is necessary to assess deal progression.
• Accurate and inaccurate reporting by salespeople can lead to misconceptions about deal status.

"In those cases, you really have to have someone engaged with that salesperson that knows what good looks like, that can weigh in on whether those deals are progressing or not."

The quote highlights the importance of having an experienced person work with new hires to evaluate the progress of deals, which is crucial in long sales cycles.

• Slipped deals are often due to a failure in the discovery stage of the sales process.
• A lack of understanding of the buyer's needs and business factors can lead to missed opportunities.
• Proper discovery is essential to connect the dots early on and ensure deal closure.

"Ultimately, this is a failure of discovery. When this happens, you can almost always trace it back to the beginning of the conversation in that deal and a lack of understanding of some key factor."

This quote emphasizes that many deals that slip to the next quarter could have been saved with a better understanding of the buyer's needs and more thorough discovery at the start of the sales process.

• Discounting can be a useful tool to create urgency and close deals if used strategically.
• Reliance solely on discounting is not advisable; other urgency-creating levers should be used.
• A balanced approach that includes terms, pricing, and addressing risks is recommended.

"If you can do discounting that way, it can be really powerful. But you've got to understand there's so many other levers to create urgency."

The quote suggests that while discounting can be effective, it should be part of a broader strategy that uses multiple tactics to create urgency and close deals.

• In a capital-constrained environment, CFOs are more involved in buying decisions.
• Sellers must engage CFOs early in the deal process to address potential objections and requirements.
• Multithreading and early engagement can help uncover the full landscape and avoid last-minute deal collapses.

"The most important thing in an environment like this is that your sellers pull those people into deals much earlier."

This quote stresses the necessity of involving CFOs and other key decision-makers early in the sales process to navigate a capital-constrained environment effectively.

• Shift in value drivers from growth to cost savings and efficiency due to changing market conditions.
• Sales strategies must adapt to emphasize different value propositions to align with customer priorities.
• Value-based selling and providing data to demonstrate ROI are becoming more important.

"We're going to have a little more emphasis on cost savings and efficiency. And yes, growth still matters."

The quote indicates that while growth remains important, there is a need to adjust the emphasis on value drivers such as cost savings and efficiency to meet changing customer expectations.

• Fundamental sales tactics such as authentic engagement and real value proposition remain unchanged.
• High volume, cold outbound sales tactics have become less effective; personalization is key.
• The biggest challenge for a Chief Revenue Officer (CRO) is adapting to rapid changes and planning for uncertainty.

"Ultimately, sales is the same as it has always been. It goes back to the Rudnitsky playbook. People buy from people."

This quote reinforces the enduring principle that successful sales are rooted in human connections and delivering authentic value.

• Speaker A sued their school district for banning a book with a homosexual theme.
• The court ruled in favor of Speaker A, requiring the school to reinstate the book and pay legal fees.

"I sued my Kansas school district because they banned a book."

The quote provides a personal background story about Speaker A taking legal action against censorship, demonstrating their commitment to principles and justice.

• New sales leaders should ask questions fearlessly and engage with executives.
• Sales should become more human and empathetic.
• The future of sales is uncertain, with potential mild or significant recessions impacting annual planning.

"Ask all the questions. No question is stupid. Ask everyone questions."

This quote advises new sales leaders to be inquisitive and proactive in seeking information and guidance from their team and executives.

• Clary's sales process impressed Speaker A due to its human-centric approach and thoughtful engagement.
• The quality of the sales process and the value demonstrated by the product were key to closing the deal.

"Clary's sales process, very human. It's very high quality. Every touch is quality and thoughtful."

The quote praises Clary's sales strategy, highlighting the importance of a human touch and high-quality interactions in the sales process.