20Sales Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

In this episode of "20 Sales" with host Harry Stabbings, the conversation centers around effective sales strategies and the evolution of sales leadership with Lori Jimenez, Chief Revenue Officer at Work Ramp. Jimenez, with a 25-year career at companies like Google and Facebook, shares insights on hiring sales teams, emphasizing the need for genuine human connection, active listening, and curiosity in sales roles. She underscores the importance of founders setting initial sales playbooks, leveraging their passion and product knowledge, and the benefits of hiring multiple salespeople simultaneously for team dynamics and culture. Additionally, Jimenez discusses the significance of mutual evaluation plans for forecasting accuracy and maintaining customer relationships post-sale, as well as the need for more female leadership in sales. Tools like Pocus and Sales Loft are also highlighted for their roles in streamlining sales processes and driving revenue.

• Assessing candidate's knowledge to determine if they're sufficiently informed ("know enough to be dangerous").
• Evaluating how candidates have been successful in the past using their experiences ("the how").
• Importance of storytelling in conveying how candidates have navigated through wins or losses.
• The necessity of utilizing different resources and strategies in challenging situations.
• The significance of asking probing questions to uncover a candidate's problem-solving abilities.

"Break down an interview process into kind of chunks. Do they know enough to be dangerous? And then the next sale in the process is the how."

The quote emphasizes the importance of structuring an interview in stages to first assess basic knowledge, followed by a deeper dive into the candidate's experience and problem-solving skills.

• Lori Jimenez is the Chief Revenue Officer at Work Ramp.
• Lori's career spans 25 years, including roles at Google, TripActions, Navan, Facebook, and Box.
• "20 Sales" is a sales-focused show hosted by Harry Stebbings, featuring insights from leading sales professionals.

"Today, I'm so excited to welcome Lori Jimenez, chief revenue officer at Work Ramp, where she's responsible for sales, customer success solutions, engineering, sales development and revenue operations."

This quote introduces Lori Jimenez and her role, setting the stage for the discussion about her extensive experience in scaling sales teams.

• Pocus is a revenue data platform aiding go-to-market teams in analyzing and visualizing data without engineers.
• Sales Loft is a sales engagement platform that assists sales teams in managing deals and improving performance.
• Both tools aim to prioritize opportunities and enhance efficiency for sales teams.

"Pocus is a revenue data platform that makes it easy for go to market teams to analyze, visualize and action data about their prospects and customers without needing engineers."

The quote highlights the functionality of Pocus, explaining how it benefits go-to-market teams by providing actionable insights from data analysis.

• Lori's sales career began at age 15 with a retail job, which sparked her interest in customer interaction.
• Post-college, Lori joined Remedy Corporation, which was later part of BMC, marking the start of her professional sales career.
• Lori emphasizes the importance of seizing opportunities and adapting to the market's needs.

"I discovered sales at the ripe age of 15 and a half, which was the day I got a worker's permit and could get a job."

This quote tells the story of Lori's early exposure to sales, which laid the foundation for her future career.

• Lori believes sales is an art and science that can be learned and appreciated over time.
• Sales involves genuine connection, active listening, and understanding customer needs.
• Even those who do not initially love sales can develop a passion for it by learning its nuances.

"I think it's the latter. And I say that even though that wasn't my experience, because I think there's a perception sometimes about sales that it is just this kind of robotic, anyone can do it, go and run a script."

The quote expresses Lori's view that sales is more than a scripted process and can be a learned skill that grows into a passion.

• Google: The necessity of building genuine connections and understanding stakeholder partnerships.
• Facebook: Focus on making an impact with small, targeted teams.
• TripActions/Navan: Comfort with moving fast and dealing with ambiguity.
• Box: Embracing ownership and feeling like an integral part of the company's success.

"The real takeaway there is the importance of building genuine connections to do great work."

This quote from Lori's time at Google stresses the importance of collaboration and building meaningful relationships to achieve success.

• A sales playbook is likened to a GPS, guiding sales processes without being overly prescriptive.
• It builds on previous sales experiences to inform successful sales motions.
• Playbooks should allow for creativity and flexibility, accommodating individual sales styles.

"Think of it as more of a gps, so it doesn't have to be a script."

The quote compares a sales playbook to a GPS, suggesting it should provide direction while allowing for individual navigation.

• Founders are best positioned to create the initial sales playbook due to their deep understanding of the product and market.
• Founders can pivot the playbook and product based on customer feedback.
• As the company grows, the playbook can evolve while maintaining the founder's insights.

"The founders are the right folks to create it for a few reasons."

This quote explains why founders, with their passion and knowledge, are ideal for crafting the initial sales playbook.

• Early-stage startups benefit from hiring driven individuals who may not have a "big logo" background.
• Junior talent can bring creativity and adaptability without being constrained by past experiences.
• The right hire should be eager to navigate challenges and contribute to building the company.

"I believe, especially in the early stages, there's a huge opportunity to not only identify and sprout new talent in a startup."

Lori argues for the potential of hiring and developing new talent in a startup environment, emphasizing the value of drive and adaptability over established brand experience.

• Hiring multiple salespeople at once has several benefits.
• It creates a team environment that fosters collaboration and sharing of sales strategies.
• Onboarding multiple salespeople at the same time is more efficient.
• A founding sales team can generate a positive culture and energy that impacts the entire company.

"I think you should hire more than one at a time for a few reasons, less about the competition. I think that's kind of going to happen."

This quote emphasizes the importance of hiring multiple salespeople not for competition but for the benefits of teamwork and efficiency in onboarding.

• The hiring process should be broken down into stages.
• The first stage is vetting for role-related knowledge to ensure candidates have the necessary skills and experience.
• The second stage is understanding how candidates have achieved success or navigated failures in the past.
• It's important to assess a candidate's reaction to challenges and their ability to work in a startup environment.
• Questions about failures can reveal a candidate's ability to learn and work with a team.

"The first part would be just vetting for, and this is a term I learned at Google, which the way just they framed it is really helpful, is like vetting for just role related knowledge."

The quote explains the initial part of the interview process, which focuses on ensuring the candidate has the knowledge and skills relevant to the job role.

• Providing data and evidence of past performance is crucial for sales candidates.
• Data demonstrates the candidate's pride in their accomplishments and their understanding of the impact they've made.
• It is also a sign of a candidate's ability to track and measure their success.

"I love it when you see, like, I increased net revenue retention by 12% through these three channels."

This comment highlights the importance of candidates providing specific data points to illustrate their achievements.

• Candidates should undergo practical exercises such as mock sales calls or case studies.
• These exercises should relate to the company the candidate is interviewing for to gauge their research skills and curiosity.
• It's important to see how candidates handle high-pressure situations and their comfort with being uncomfortable.

"I like to have some sort of case study discovery call whatever it might be that's on the company that they're going to interview."

The quote stresses the value of having candidates perform practical tasks related to the company to assess their research capabilities and how they handle the pressure.

• Compensation discussions can reveal a candidate's motivations and alignment with the company's values.
• Titles can be important for candidates' career progression or external accreditation, but they must be managed to avoid future title inflation issues.
• It's sometimes necessary to let a candidate go if their focus is too heavily on compensation over other factors.

"I think it's a moment to really understand what someone's motivations are and also just see kind of where their research went."

This quote discusses using compensation discussions to understand a candidate's true motivations and whether they align with the company's mission.

• Shallow, canned responses are a red flag in interviews.
• Lack of depth in answers, especially regarding teamwork and customer engagement, can indicate a lack of genuine experience.
• It's important to vet the candidate's approach to challenges and their readiness for a startup environment.

"If the answers just are shallow, if they're just very canned and shallow and you feel like, okay, I could play back a bunch of different LinkedIn posts and collect a bunch of these, and this would be an answer."

This quote points out that superficial answers in an interview can indicate a lack of substance and real-world experience.

• Not vetting the "how" behind a candidate's ambition can lead to hiring mistakes.
• Relying too heavily on references without seeking deeper insights can be problematic.
• It's common for candidates to overestimate their readiness for the startup environment.

"I've had folks that it came off in an interview were super ambitious. Right? They're like, I'm going to do this, I'm going to build this iI. And they had this energy about them. But when you really peeled back how they're going to do it, not vetting the how enough."

The quote illustrates the issue of being swayed by a candidate's ambition without properly assessing their ability to execute on their plans.

• Curiosity and the ability to ask informed, follow-up questions are key traits of successful salespeople.
• Active listening involves paying attention to both positive alignment and potential roadblocks.
• Sales teams should be trained and enabled to practice active listening.
• Perfect calls are highlighted within teams to provide concrete examples of successful sales interactions.

"One of the most important characteristics, in my opinion, with a great salesperson is being curious."

This quote emphasizes curiosity as a crucial trait for a salesperson, which is directly related to their ability to actively listen and engage with clients effectively.

• Sales can be perceived as robotic when reps treat it as a checklist process rather than a conversational engagement.
• The importance of actively listening and engaging with the customer's response to questions is emphasized.
• The goal is to avoid wasting both the customer's and the salesperson's time by not gaining anything from the experience.

"It goes back to that perception sometimes of sales, it being just a kind of robotic method. It's like, no, there's a list and we might give you that to help guide you, but that is not meant to be just something you kind of check, check, because then you're wasting the customer's time and you're wasting your own time because you didn't get anything from that experience."

This quote highlights the issue of sales reps not utilizing the provided questions effectively, treating them as a mere checklist rather than a tool to deepen understanding of the customer's needs.

• Aligning discovery with the output desired for the goal can manipulate the effectiveness of sales development representatives (SDRs).
• The use of qualification criteria, such as BANT (Budget, Authority, Need, Timeframe), is recommended to ensure quality leads.
• Sales stage progression incentives can validate the quality of opportunities created by SDRs.

"And I think the way to mitigate that is a few ways, is having a qualification criteria that has to be met."

This quote suggests that establishing clear qualification criteria is essential to setting effective goals for SDRs, ensuring that they focus on quality over quantity.

• Key performance indicators include pipeline acquisition and acceleration.
• The importance of a sales rep's ability to take feedback and learn from it is highlighted.
• A lack of learning or improvement after coaching and resourcing is a red flag.

"So I think you have to go back to pipeline acquisition and pipeline acceleration."

The quote emphasizes the necessity for sales reps to focus on both creating new opportunities and advancing existing ones in their pipeline.

• Confirming mutual agreement on execution timelines with prospects is crucial.
• Understanding the reason behind a deal being pushed to the next quarter is necessary, such as internal events or lack of access to the economic buyer.

"So the first question would be, did you have mutual agreement with the prospect on when we would execute?"

This quote underlines the importance of having a clear and mutually agreed upon timeline with the prospect to avoid unexpected delays in deal closure.

• Discovery should involve identifying stakeholders, budget sources, and organizational priorities.
• Building value and connection with the economic buyer reduces the risk of being consolidated against.

"Well, I think you start from doing the discovery with your champion and coach to understand who are the stakeholders who ultimately signs, whose budget does it come from and how does this fit into their priorities?"

The speaker stresses the need for thorough discovery to ensure engagement with the actual decision-maker who has financial authority.

• Multithreading is crucial but should be done with the buy-in of the champion.
• Explaining the 'why' behind engaging with multiple stakeholders is important.
• It's beneficial to show how multithreading can amplify the champion's goals and career path.

"First get the buy in for the champion of why it's so important in every sales engagement, explain the why."

The quote highlights the strategy of securing the champion's support before attempting to engage with additional stakeholders in the organization.

• Traditional face-to-face enterprise selling methods have not completely died but have been adapted.
• The pandemic has shifted the focus towards virtual selling, though in-person engagement can still add value.
• Understanding the buyer's preferences is key to deciding on the appropriate sales approach.

"I don't think it's fully dead. It was the play when like that was know, you flew out to Texas, you took them to the steakhouse, you did all that stuff."

This quote reflects on the shift in sales methods due to COVID-19, suggesting that while traditional methods have changed, they still have a place in certain scenarios.

• Discounting may be necessary in competitive markets to gain a foothold.
• Discounts should come with a value trade-off, such as customer references or introductions.
• Transparency about discounts during the proposal stage is important.

"I think it's all about a trade off. It's like, what are you demonstrating from a value trade for that?"

The quote implies that discounting should not be arbitrary but should serve as part of a strategic exchange that benefits both the customer and the company.

• Multi-year deals are favorable for gross retention.
• Financial incentives can make multi-year deals compelling for both the customer and the vendor.
• Sales teams can be incentivized to pursue multi-year contracts.

"Yeah, I mean, multi year deals right now especially are a good thing."

The speaker advocates for multi-year deals, emphasizing their benefits for sustained business relationships and revenue retention.

• Customer testimonials should be sought after proving value to the customer.
• Setting expectations for testimonials is important, with the understanding that the company will meet its commitments.
• Maintaining a long-term, genuine relationship with the customer increases the likelihood of obtaining testimonials.

"But I think it's important to ask. But I think important to set the framework is like, we're going to meet the mutual goals that we agreed on."

The quote suggests that customer testimonials should be part of a reciprocal relationship where the company delivers on its promises before requesting a testimonial.

• The handoff from sales to customer success should not feel dehumanized.
• Involving the implementation manager early and maintaining the account executive's involvement post-sale is crucial.
• Compensation structures can incentivize continued engagement with the customer.

"So we don't operate as a sales organization and an implementation organization and a success organization and a support organization. It's one."

This quote emphasizes the importance of a unified approach across different departments to maintain a consistent and humanized customer experience throughout their journey.

• QBRs are a regular business review with a customer to assess progress against set goals.
• They are not just check-ins but opportunities to show data-driven progress and suggest new strategies.
• QBRs should be a moment of validation for original goals and a platform to add value.
• The frequency of QBRs can vary, but regular scheduling is crucial.

So quarterly business review and there's argument to do quarterly or monthly, but essentially a regularly scheduled business review with your customer that demonstrates how they are progressing against the goals we originally set.

This quote emphasizes the purpose of QBRs as a means to regularly assess and demonstrate customer progress against predetermined goals.

• Customer success is about staying connected with the customer beyond the sale.
• Anticipating churn involves looking for signals and measuring customer health using both data and anecdotal experiences.
• Interventions may be needed to re-engage customers who are showing signs of disengagement.

Yeah, you've got to look for signals. And then some of it is subjective, of course, because anticipation is going to come from a customer success manager connecting with a customer and like, reading that experience and figuring out what does that mean.

This quote highlights the subjective nature of anticipating churn, which relies on the customer success manager's ability to read and interpret customer experiences.

• Deal reviews should be based on a common framework known to the team.
• They are meant for learning and diagnosing, not for storytelling or defensive posturing.
• The goal is to identify resources and support needed to accelerate deals and address gaps.

I think what's important is a good deal review is based on a common framework.

This quote underscores the importance of having a structured approach to deal reviews that everyone understands.

• A good reason to lose a deal is a genuine mismatch in customer needs and product offerings.
• A bad reason is underestimating competition or not understanding the customer's core goals.

I think a good reason is if there really is just a mismatch in what the customer needs from a feature perspective.

This quote explains that losing a deal is acceptable if the product does not align with the customer's needs, as this prevents future churn.

• Forecasting requires accountability and consistent scrutiny of forecasts, regardless of whether the quarter is high or low.
• High volatility in the market requires a healthy skepticism in deal assessment.

Back to that balance of you have to set the foundation that there's going to be a level of accountability to the forecast.

This quote stresses the importance of maintaining a consistent level of accountability in sales forecasting.

• Core sales tactics involving good listening and providing value have not changed.
• Onsite sales meetings are becoming less common due to the effectiveness of virtual engagement.
• Setting clear expectations is crucial when hiring sales teams.

I would say selling is an art and a science, but at its core it's about really good listening and bringing value.

This quote points out that despite changes in sales tactics, the fundamental aspects of good listening and value delivery remain unchanged.

• New sales leaders should deeply learn the business in the first 90 days but be prepared to relearn with additional context.
• Continuous learning is essential for sales leaders.

I would give them the advice, like really dig in and learn in those 1st 90 days deeply, but be prepared to relearn everything at 90 days.

The quote advises new sales leaders to immerse themselves in learning the business initially but to stay adaptable and ready to integrate new insights.

• There is a desire for more female leadership in sales, despite improvements over the years.
• Continued focus on gender diversity in leadership positions remains a priority.

This has changed tremendously in my career, but I would like to see more female leadership at the top.

This quote reflects the speaker's wish for increased female representation in sales leadership roles, acknowledging progress but recognizing the need for ongoing effort.

• Clear communication and post-sale engagement are key components of an impressive sales strategy.
• The speaker was impressed by Vitally's sales strategy due to their consistent communication and dedication to customer success post-sale.

What I was really impressed with is really clear communication the whole way and very direct and engaging.

This quote praises Vitally for their clear and engaging communication throughout the sales process and beyond.