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Lori Jiménez: How to Increase Sales; Hiring Tips from Google; Best Way to Grow Sales Teams | E1043

Lori Jiménez is the Chief Revenue Officer at WorkRamp where she is responsible for sales, customer success, solutions engineering, sales development, and revenue operations. Over her 25-year career, Lori has a track record of scaling high-growth GTM teams at companies including Google, TripActions/Navan, Facebook, and Box. ------------------------------------------------------------------------ Timestamps: 00:00 Intro 00:21 Lori's Sales Journey 07:57 Developing Sales Playbooks 11:22 Building Sales Teams 21:21 Sales Techniques and Success 31:36 Aligning Goals and Sales Rep Performance 35:42 Relationship Building and Sales Growth 39:31 Strategies for Sales Growth 53:23 Quick-Fire Round ------------------------------------------------------------------------ In Today’s Episode with Lori Jimenez We Discuss: 1. From a First Sales Job at 15 Years Old to Leading Sales Teams at Google and Facebook: How Lori made her foray into the world of sales at the age of 15? What are 1-2 of Lori’s biggest takeaways from her time at Google, Facebook and Box? What does Lori know now that she wishes she had known at the start of her career in sales? 2. The Sales Playbook: What, When and How: How does Lori define the “sales playbook”? What is it not? Should the founder be the one to create the sales playbook? When is the right time for founders to make their first sales hires? What is the right profile for the first sales hires? Should founders hire 2 sales reps at a time? What are the pros and cons? 3. The Hiring Process: Building the Sales Team: How does Lori structure the hiring process for all new sales hires? What are the must-ask questions to ask in every sales hiring meeting? What are the biggest red flags founders should look for when hiring for sales? What are Lori’s biggest lessons on how to navigate compensation discussions with potential sales hires? What are Lori’s biggest lessons on what title negotiation says about a candidate? What are the single biggest mistakes founders make when hiring for sales teams? 4. Scaling the Machine: Bringing the Dollars In: How does Lori approach discounting? When is the right time to do it? Is old-school enterprise sales and entertaining dead? How has it changed? How does Lori structure deal reviews? What is a good vs a bad reason to lose a deal? How does Lori approach multi-year deals? What is good? What is bad? ------------------------------------------------------------------------ Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ------------------------------------------------------------------------ #LoriJimenez #Workramp #HarryStebbings

Lori JiménezguestHarry Stebbingshost
Aug 1, 202357mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Lori Jiménez Reveals How To Build, Hire, And Scale Sales Teams

  1. Lori Jiménez, veteran sales leader (Google, Facebook, Box, Navan, WorkRamp), shares how to design sales playbooks, hire early sales talent, and build predictable revenue organizations.
  2. She argues founders must own the first sales playbook, avoid over-indexing on ‘logo hires,’ and instead prioritize curiosity, grit, and coachability in early reps.
  3. The conversation goes deep on interviewing and compensation for sales roles, onboarding, discovery and active listening, deal reviews, discounting, and forecasting in volatile markets.
  4. Throughout, she stresses genuine human connection, cross-functional collaboration, and a revenue-team mindset that tightly links sales, implementation, and customer success.

IDEAS WORTH REMEMBERING

5 ideas

Founders should own the first sales playbook before hiring sales leaders.

Because they know the product, customer problem, and ‘why’ more deeply than anyone else, founders are best placed to craft the initial narrative, iterate based on feedback, and then hand a proven motion to a head of sales.

Don’t overvalue ‘logo hires’; prioritize scrappy, curious, and adaptable talent.

Big-brand résumés can mask rigidity and misfit; early-stage companies need people energized by ambiguity, willing to build from scratch, and open to new ways of selling rather than importing a single ‘right way’ from a prior employer.

Interview for ‘how’ they win and lose, not just that they win.

Dig into losses, team collaboration, and specific metrics; shallow, scripted answers and excessive ‘I, I, I’ are red flags, while detailed stories with data and cross-functional teamwork indicate mature, repeatable performance.

Active listening and structured discovery are core sales superpowers.

Great reps ask layered questions, listen for both desired and undesired answers, and adjust in real time; managers should coach this by reviewing calls, highlighting ‘perfect’ discovery examples, and discouraging robotic scripts.

Align SDR incentives with quality, not just volume.

Using clear qualification frameworks (e.g., BANT/MEDDIC) and tying some SDR credit to opportunity stage progression ensures they don’t just ‘book meetings’ but hand off pipeline that sales can actually advance.

WORDS WORTH SAVING

5 quotes

One of the most important characteristics of a great salesperson is being curious.

— Lori Jiménez

Think of a sales playbook as a GPS, not a script.

— Lori Jiménez

You can’t do anything on your own at Google… the stakeholder partnerships you make are critical to how you get work done.

— Lori Jiménez

We don’t operate as a sales organization, an implementation organization, and a success organization—it’s one revenue organization.

— Lori Jiménez

Forecast inspection needs to happen in the best of quarters and in the worst quarters; if you only do it when you’re down, it’s fear-based.

— Lori Jiménez

Lori’s career path and lessons from Google, Facebook, Box, Navan, and WorkRampWhat a good sales playbook is and why founders must write it firstHiring early sales reps: process, red flags, compensation, and titlesActive listening, discovery, and call quality (using tools like Gong)Structuring SDR goals, qualification, and preventing ‘fluffy’ pipelineCustomer success handoffs, QBRs, health scores, and churn predictionDeal reviews, discounting, multi-threading, multi-year deals, and forecasting

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