Aug 2, 2023 · 57m · news
Lori Jiménez: How to Increase Sales; Hiring Tips from Google; Best Way to Grow Sales Teams | E1043 · 20VC with Harry Stebbings
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In this episode of 20VC, Harry Stebbings interviews seasoned sales executive Lori Jimenez, exploring the tactical blueprints for building customer-centric sales playbooks, optimizing startup hiring strategies, and executing predictable enterprise sales execution.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 19.3% of the talking time here. How this is scored →
Harry as informed peer 4.4 Guest teaching 3.8 Guest disagreement 0.9 Harry pushing back 1.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 41:46 Lori pushes back on contractual mandatory testimonials
Lori directly disagrees with Mark Goldberger's policy of contractually requiring testimonials, insisting that sales teams must prove value first before demanding public advocacy.
Hardest push from Harry ▶ 28:00 Harry rejects 'warm and fuzzy' sales buzzwordsHarry explicitly calls out Lori's abstract phrasing around active listening and human connection, demanding tangible operational proof of how those concepts are implemented.
Biggest teaching moment ▶ 34:39 Lori explains why deals slip and how rep oversight causes delaysLori educates Harry on why deals get pushed into future quarters, showing how lack of joint evaluation plans and missing access to economic buyers are the real root causes.
Harry holds his own ▶ 24:35 Harry explains title inflation as external sales accreditationHarry demonstrates keen GTM domain knowledge by explaining how inflated titles give reps needed leverage and credibility when negotiating with enterprise buyers.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Lori Jiménez's Journey into Sales | 2 | 1 | 0 | 0 | Harry opens with a warm welcome and asks Lori how she entered the world of sales. Lori shares her story of working in retail at 15 and moving into software sales at Remedy Corporation during the 90s recession. | |
| Can You Learn to Love Sales? | 3 | 3 | 1 | 1 | Harry asks if sales is an instant love or something learned over time, expecting instant, but Lori gently reframes that learning to love sales is more common. Harry then asks for rapid takeaways from her time at Google, Facebook, Navan, and Box. | |
| Defining a Sales Playbook | 5 | 4 | 0 | 2 | Harry asks Lori how she defines a sales playbook and who should author it. Harry asserts his view that a founder must understand their own playbook before hiring a head of sales. | |
| The Ideal Profile and Timing for Early Sales Hires | 5 | 4 | 1 | 2 | Harry questions Lori on hiring hungry up-and-coming reps versus logoed enterprise veterans and asks whether the motion changes for PLG versus enterprise. Lori highlights how junior scrappy reps bring hunger while enterprise motions require more gravitas. | |
| Hiring and Onboarding Sales Reps in Pairs | 6 | 3 | 1 | 3 | Harry cites Jason Lemkin's hiring philosophies and asks Lori to detail an interview process. Harry interjects with a firm preference for having candidates perform case studies on the hiring company rather than a random third party. | |
| Navigating Compensation and Titles in Sales Hiring | 5 | 3 | 1 | 2 | Harry explores compensation and title negotiations with prospective hires. Harry counters standard title suppression advice by explaining that inflated titles give enterprise reps external accreditation needed to close deals. | |
| Interview Red Flags and Hiring Mistakes | 5 | 3 | 1 | 2 | Lori discusses red flags in interviews and her past hiring mistakes. Harry points out that young founders often suffer from insecurity and default to hiring recognizable corporate logos as a safety blanket. | |
| Onboarding, Active Listening, and Call Vetting | 4 | 5 | 1 | 3 | Harry playfully pushes back on Lori's phrase 'active listening and genuine human connection', asking for concrete operational metrics. Lori outlines Gong call auditing and call scorecard channels. | |
| Aligning SDR Goals with Sales Outcomes | 5 | 4 | 1 | 2 | Harry points out how discovery goals for SDRs can be gamed to hit quotas rather than deliver real pipeline. Lori explains tying SDR incentives to downstream sales stage progression to prevent metric manipulation. | |
| Navigating Delayed Deals and Identifying Economic Buyers | 5 | 5 | 1 | 2 | Harry brings up board meeting frustration over deals continually pushed to next quarter and asks how to spot chest-pumping champions. Lori breaks down economic buyer access and joint evaluation plans. | |
| Multi-Threading and Relationship Building in Enterprise Sales | 4 | 4 | 1 | 1 | Harry asks how to multi-thread without offending contacts and asks whether traditional lavish enterprise entertainment is dead. Lori explains how to align multi-threading with champion career progression. | |
| The Ethics and Tactics of Discounting and Testimonials | 5 | 4 | 2 | 2 | Harry brings up Mark Goldberger's strategy of mandating customer testimonials in standard contracts. Lori offers a mild pushback, arguing testimonials must be earned by first demonstrating value. | |
| Managing Customer Handoffs and Structuring QBRs | 4 | 5 | 1 | 2 | Harry questions how to prevent account handoffs from feeling transactional and dehumanized. Lori shares how her teams operate as unified revenue orgs where AEs attend implementation kickoffs and QBRs. | |
| Anticipating and Mitigating Customer Churn | 4 | 5 | 1 | 1 | Harry asks how to spot customer churn before it happens and how to conduct effective deal reviews. Lori explains combining qualitative engagement signals with quantitative health data and keeping deal reviews focused on gaps rather than story time. | |
| Analyzing Good vs. Bad Sales Losses | 5 | 5 | 1 | 1 | Harry asks Lori to differentiate between a good loss and a bad loss, as well as how to maintain sales forecast accuracy during market downturns. Lori advocates inspecting forecasts with equal rigor during good quarters as bad ones. | |
| Quick-Fire Insights: Sales Tactics, Hiring Mistakes, and Favorite Strategies | 3 | 3 | 0 | 0 | Harry runs through a rapid-fire round covering enduring sales principles, dying tactics, founder mistakes, and female representation in executive sales roles. Lori closes by praising customer success platform Vitally. |
Statements from this episode (28)
Jiménez: Curiosity and active listening are key traits of great salespeople
“One of the most important characteristics, in my opinion, with a great salesperson is being curious. It's someone who can ask a question, who can ask the next question that's connected to that first question. Really listen to the first answer, not just for the…”
Lori Jiménez: Top Sales Performers Usually Learn to Love Sales Over Time
“Honestly, 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 like kind of robotic, anyone can do it, go and run a script. And there's not a lot of huma…”
Jiménez: Google's size prevents individual execution without broad stakeholder partnerships
“You can't do anything on your own at Google. It is so big. It's so complex. There's so many layers and crossover of teams and initiatives and budgets and structures that you have to learn quickly that the stakeholder partnerships you make are critical to how y…”
Jiménez: Sales playbooks should act as guides, not rigid scripts
“A playbook should be a, think of it as a more of a GPS. So it doesn't have to be a script, like each step down to the minute detail. I'll think of it as a guide. So depending on where you are in a sales process where there it's very early and you're doing disc…”
Jiménez: Founders, not the head of sales, must build initial sales playbooks
“I think the founders are the right folks to create it for a few reasons.”
Jiménez: Early startups should hire junior sales talent over big tech logos
“So I'm a big believer in you can really do great things with maybe a more junior, perceived junior talent because of the creativity they can bring, and they don't have kind of a bias from a previous experience.”
Lori Jiménez: Founders should hire sales reps only after proving repeatability
“So I think it's that moment where you find a repeatable, you've got enough customers and you find enough of a repeatable process that can take your good work and grow it, you know, and take and get and have feedback.”
Jiménez: Startups should hire sales reps in batches, not individually
“I think you should hire more than one at a time for a few reasons. Less about the competition. I think they're, you know, that's kind of going to happen maybe naturally, but it's more about you can work. It's work for scale. I think if you're onboarding one pe…”
Jiménez: Excessive 'I' usage in sales candidate interviews is a red flag
“If you hear too many mentions of I mean, of course it's sales and you want folks to be proud of their performance, but if it's too much on just what they did independently, for me, that's a red flag because I think no one wins, you know, independently. It's a …”
Jiménez: Sales case studies should evaluate candidates on the hiring company
“I like putting in front of the candidate about the company they're gonna come join, not because I'm looking for like, The perfect answer, but more I like that they just do go and do homework. Like how are they curious? Like are they, it demonstrates if they're…”
Jiménez: Sales candidates focused solely on cash OTE lack startup staying power
“And if it comes down to just a dollars on OT, I'm always a little bit like, that's a little, it's not a full red flag depending on, you know, where the conversation goes, but it's something that I concerns me because that will come back You know, in the future…”
Jiménez: Inflated titles for early startup hires create future organizational problems
“It's a very individual conversation, but I also think it's important to keep in mind, and this is hard to do what you're setting up For will impact the future. So if you get too aggressive on title, then you're a couple of years down the road and your next per…”
Stebbings: Young founders make big-tech logo hires out of personal insecurity
“The most common I see with young founders is actually an insecurity in themselves of their lack of Experience, which leads to what you said earlier, which was the logo higher. They look for the Salesforce logo because they're aware that they don't have that ex…”
Jiménez: WorkRamp shares exemplar sales calls publicly in Slack
“So for example, with my current team, we do a lot of real listening of calls. Like we just, and we publicly in a Slack channel, mark them when they're perfect. And we say, this is a perfect call. And we want to highlight why this is perfect.”
Jiménez: Incentivize SDRs on sales stage progression to ensure high lead quality
“And I think the way to mitigate that is a few ways is having, you know, a qualification criteria that has to be met. So if it's a band, if it's a, you know, whatever the structure is that identifies kind of the core drivers of that call. But also I think what …”
Jiménez: Sales reps must generate a portion of their own pipeline
“But I do think it's very important for sellers to create
Some of their own pipeline. They're not fully responsible for it, but they have to have skin in the game on creating pipeline.”
Lori Jiménez: Lack of economic buyer access is top cause of deal delays
“So a lot of the core of that, like if it's A result of the salesperson's engagement. It's because there wasn't access to the economic buyer. That's usually like the number one part of medic that makes it fail is you're just not, you're not there.”
Jiménez: Multi-threading requires securing buy-in from primary champion first
“First you got to get the buy-in with the champion instead of like going around and trying to meet a bunch of people, you know, going on LinkedIn to figure out who else in this company do I know? It's like first get the buy-in from the champion of why, like it'…”
Jiménez: Traditional wining-and-dining enterprise sales is now purely additive to virtual selling
“I don't think it's fully dead. I mean, it was the play when I started. Like, that was it. You know, you flew out to Texas, you took them to the steakhouse, you did all that stuff, right? I think with COVID and realizing what we can do remote, that is Absolutel…”
Jiménez: Early-stage sales discounts must always be traded for references or referrals
“I think it's all about a trade-off. It's like, what are you demonstrating from a value trade for that? Is there something that, Hey, I'm going to give you this discount, but exchange for that especially in the early stages, I need references. You know, I need …”
Jiménez: Upfront agreements for customer testimonials must depend on proving value
“I think you have to, that's bold, but I think you have to and I'm a big fan mark, but you have to say there's a caveat around that. Like we've got to prove value. So we've got to prove what we've been telling you for whatever this selling motion period is. We'…”
Jiménez: Account executives should attend QBRs to show ongoing customer commitment
“I think the account executive needs to join those QBRs. They need to listen. They need to participate. They need to not be maybe the one driving the QBR that the customer success manager is leading, but they need to show up. And what that shows is like, I care…”
Jiménez: Combine qualitative signals with usage data to spot churn risk
“Take that information, marry it with the customer data. If both are down, that's a signal that you could be stepping into an area of risk.”
Jiménez: Use title-matching executive outreach to re-engage unresponsive accounts
“Go title match, go to their leader and try to get a call and kind of shake something loose that oftentimes can do it. Cause sometimes it's just the person below who doesn't have the time, right? So they just need someone to kind of bump it up on their priority…”
Jiménez: Sales deal reviews must identify process gaps, not be story time
“Also deal review should not be story time. I always say this. It's not your time to tell me a story like Don't say, oh, I met with this person who's connected to this person. I talked to this person. This is what we said. And they said this, I was like, no, I …”
Jiménez: Bad sales losses stem from poor customer discovery against competitors
“Bad reason loses. You didn't anticipate the competition and how they were engaged or how much the competition was positioning, like what really the customer cared about how the competition could answer that question and how we could answer that question. So it…”
Jiménez: Sales forecast inspections must happen in good quarters, not just bad
“So oftentimes you'll see like the forecast inspection happens when you're having a down quarter forecast inspection needs to happen In the best of quarters, because if you just only pivot to when you're down, then it's in a fear based moment and you're making …”