May 10, 2024 · 1h 2m · news
Larry Shurtz: How to Hire, Train & Retain the Best Vertical Teams | E1151 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, host Harry Stebbings interviews Genesys CSO Larry Shurtz to explore the blueprint for modern sales leadership, focusing on empathetic management, selective hiring practices, and the strategic alignment of sales and customer success.
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 19.9% of the talking time here. How this is scored →
Harry as informed peer 3.8 Guest teaching 4.0 Guest disagreement 2.3 Harry pushing back 3.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 50:45 Larry interrogates Harry during slipped deal roleplay
Larry fully steps into an intense sales leader persona, grilling Harry with rapid-fire questions about his slipped deal until Harry breaks roleplay character.
Hardest push from Harry ▶ 28:44 Harry rejects putting green reps before major clientsHarry forcefully rejects Larry's suggestion of exposing new AEs to major clients early, arguing it causes panic for $500k customers.
Biggest teaching moment ▶ 37:23 Larry reframes Chris Degnan's anti-CS thesisLarry educates Harry on why Snowflake's anti-CS stance is specific to consumption models, explaining that titles differ from actual account management roles.
Harry holds his own ▶ 27:34 Harry proposes support training for onboarding empathyHarry introduces an actionable onboarding tactic regarding customer support that Larry openly admits he had not considered and will steal.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome and Larry’s Sales Origin Story | 2 | 3 | 0 | 1 | Harry introduces Larry, citing specific Salesforce metrics (1,300-person team to $2.1B revenue), establishing context before asking about Larry's sales origin story and initial prioritization lessons. | |
| Larry’s Core Leadership Framework | 3 | 4 | 1 | 3 | Harry sets up a roleplay scenario and prompts Larry with potential framework options (focusing on top accounts vs. top reps), allowing Larry to present his three-part leadership framework. | |
| The Un-Trainable Art of Sales: EQ and Empathy | 4 | 4 | 2 | 5 | Harry directly challenges the idea that sales remains 60% art, citing Gong recordings, analytics, and outbound tools to argue that only EQ remains as art. Larry politely validates and expands on EQ and empathy. | |
| Structuring a Fast and Clear Hiring Process | 2 | 4 | 1 | 1 | Harry asks how to structure a hiring process, and Larry explains why panel interviews are ineffective and why speed combined with small interview teams works best. | |
| The Danger of Compressing Timelines for "Hot Candidates" | 4 | 4 | 3 | 5 | Harry asks if he can skip steps for a hot candidate. Larry turns the questions back on Harry in a roleplay, prompting Harry to push back on candidate pressure and rushing hiring timelines. | |
| Interview Questions: Track Record, Culture, and Drivers | 3 | 4 | 1 | 2 | Harry roleplays as a candidate claiming to be a comp machine motivated solely by money, prompting Larry to demonstrate how he digs deeper to uncover true personal motivators. | |
| Case Studies and the "Who Would You Bring?" Tactic | 4 | 3 | 1 | 2 | Harry introduces his preferred interview tactic of asking candidates who they would bring with them on day one. Larry enthusiastically agrees and elaborates on network evaluation. | |
| Structuring Compensation Discussions | 5 | 4 | 2 | 4 | Harry references a recent tweet by Jason Lemkin about a top rep quitting despite making $800k. Larry reframes the story, noting she left her boss rather than the money. | |
| Modern Onboarding: Empathy Through Customer Support | 6 | 2 | 1 | 3 | Harry suggests using customer support calls during onboarding to build rep empathy. Larry is genuinely impressed and explicitly admits he will steal the suggestion. | |
| Pairing New Hires and Onboarding Red Flags | 5 | 4 | 3 | 6 | Larry suggests putting unramped reps in front of customers quickly. Harry strongly pushes back, arguing it creates panic for high-value enterprise clients. | |
| Identifying Bad Hires and Moving Quickly | 5 | 4 | 2 | 4 | Harry quotes Max Levchin ('when there is doubt, there is no doubt') to question whether bad hires should be fired in 30 days, prompting Larry to explain mental vs physical errors. | |
| Dealing with Arrogant Top Performers | 4 | 4 | 5 | 5 | Harry roleplays an arrogant, high-performing rep who charms clients but treats colleagues poorly. Larry directly counters that such reps lack self-awareness and are replaceable. | |
| Unpacking Customer Success (CS) Roles and Models | 5 | 6 | 4 | 5 | Harry cites Snowflake CRO Chris Degnan's anti-CS stance. Larry dismantles the premise by explaining how consumption models differentiate roles from titles. | |
| Verticalization and Account Scale | 4 | 5 | 3 | 5 | Harry questions why vertical playbooks have to be expensive, suggesting a junior rep become a nerd on an industry. Larry details why full technical and support vertical alignment drives cost. | |
| Discounting Dynamics and Strategic Sales Forecasting | 3 | 4 | 3 | 3 | Harry asks about discounting strategy to win logos. Larry bluntly declares his hatred for discounting without clear business value justification. | |
| Roleplay: Slipped Deals and Forecasting Accuracy | 4 | 5 | 6 | 4 | Harry roleplays an AE reporting a slipped deal. Larry aggressively interrogates him as a sales leader, forcing Harry to humorously break character. | |
| The CFO Centralization Excuse and Larry’s Early Empathy Failures | 4 | 4 | 3 | 4 | Harry presents the common excuse that CFOs have centralized budgets, nudging Larry to call bullshit. Larry balances macroeconomic empathy with high seller accountability. | |
| Improving as a Leader: Lessons from Godfrey Sullivan | 2 | 4 | 0 | 1 | Harry asks Larry about moments of leadership growth. Larry shares personal reflections and lessons learned from former Hyperion CEO Godfrey Sullivan. |
Statements from this episode (33)
Shurtz: Inaccurate sales forecasting reveals poor business understanding or diligence
“If you can't forecast accurately, either you don't truly understand your business, you aren't truly doing the amount of diligence with customers and opportunities, you don't have enough opportunities to be able to balance out some of the riskier things with so…”
Shurtz: Overcommitting as a sales leader causes severe health and mental strain
“If you're personally trying to do too much, you know, this is where you really get into what I would think are, or what I know are mindset challenges. These end up in health challenges. You really get spread way too thin when you're trying to do too much”
Shurtz: Adding sales priorities without removing old ones breaks team execution
“When you're when you're like, it's a very diminishing trait when you try and do too much, my opinion, because you flow it down and you keep adding things on. You never take anything off. Like the list just kind of keeps growing. And when the list grows, your t…”
Shurtz: Sales is 60% inherent talent and 40% learned skill
“I, today, am probably in the sixty-forty, if you press me, I still think it's a lot of art. I still think it's a lot of talent, and when I say talent, I'm talking things that you and I, like, that, that, it's hardwiring. That hardwiring was, when we turned 13,…”
Larry Shurtz: High-end EQ and empathy cannot be trained
“The, in my opinion, the things you cannot train EQ. Really, really good high-end EQ. I just, I firmly believe that that's in you. And I think that is the art, and I would tell you, as it relates to things like empathy, which is what we're all looking for from …”
Larry Shurtz: Effective sales playbooks start with outcomes and work backward
“I always start playbooks with like outcome, outcome first and work backwards, right? Because I think you can get play super playbook happy. Super playbook heavy. Everybody's got a playbook. Playbooks end up conflicting with each other.”
Larry Shurtz: Hiring failures stem from role ambiguity, not talent deficits
“I have a high confidence score that when you aren't clear about what you want, what you specifically want, That's when you may end up missing and hiring the wrong person has very little to do with whether that person was talented or not. It has to do with, hav…”
Larry Shurtz: Panel interviews are ineffective for assessing sales candidates
“I'm not a fan of panel interviews. I like doing interviews one-on-one. I strongly advocate that for my leaders because the relationship between the people that you work with for and around really matters, and I think that's difficult to get out of a panel.”
Shurtz: Rushing candidate diligence leads to costly 12 to 18-month hiring mistakes
“I think this is where a lot of hiring mistakes are made because you do not do enough diligence and the challenge is compounded globally because in some markets you hire the wrong people. That could be a year to an 18 month process to get a new person back in s…”
Shurtz: Candidates demanding rapid offers via leverage fail value alignment tests
“I don't like the hostage negotiation strategy of, Hey, I got a bunch of offers. You know, you need to get me one in the next week. That's probably not the, like, especially if it's that language, That person doesn't match our value statement anyway. Certainly …”
Larry Shurtz: A 45-minute interview reveals candidate mindset better than case studies
“There is a lot of value sometimes out of the case study, but for me, the case study gets to what is your mindset and your thought process. It gets to the what and the how. And I don't know, like, I feel like I can get that out of talking to you for 45 minutes.”
Shurtz: Discuss Compensation Expectations Mid-Process, Not at the End
“I like to know that we can afford someone and get to a comp structure before, like, it's time to have a comp discussion. I think you need to do that sooner rather than later. I don't, it's not the first conversation. It's not the last conversation.”
Shurtz: Empathetic servant leadership drives sales loyalty more than compensation
“The impetus on leadership these days, and the impetus on what I think is like true servant leadership, I think that is driving more loyalty. You know, you can wrap empathy into this as well. I think those are, for most people, and I could be completely wrong o…”
Shurtz: Corporate onboarding will never return to pre-COVID in-person defaults
“We will never rotate all the way back to the way it was, and I'm talking a little bit about, like, in-person versus digital or remote.”
Shurtz: Initial employee onboarding must be in person to convey culture
“I think the initial indoctrination or immersion And if that's a safe word to use needs to be in person. I don't think there's a better way to communicate the culture of the company to interface with important objectives, to talk and meet with executives.”
Stebbings: Listening to support calls best trains sales empathy
“It is the most effective thing that I urge all founders with sales teams to hear the pains of customers. You hear, you speak about training empathy. It's probably the closest way to train empathy, just to listen to the customer support.”
Larry Shurtz: New sales reps should never meet clients alone
“I wouldn't send you a loan as a new AE. I would send you with either your boss or someone else”
Larry Shurtz: Trust interview gut feelings as doubts usually manifest as problems later
“I hear that a lot with people and I, my advocacy is trust your gut. Normally those things will show up. Later and without fault. The hiring mistakes that I've made end up showing up in our example right now that were things that I didn't feel a hundred percent…”
Larry Shurtz: A bad hire is multiple red flags plus coaching failure
“Bad, bad is the sum of a lot of red flags and a lack of improvement with coaching.”
Shurtz: Sales teams identify bad hires before leaders do
“By the time the leader knows it, everyone else on the team knows it. They know it before you do.”
Shurtz: Abrasive sales candidates will treat customers badly
“Do I ever hire people that I don't like where I'm like, oh my God, like, I just don't like that person. They're offensive. They're abrasive. No, I just don't even hire them. Because if they're that way to me, they're going to be that way with our customers.”
Shurtz: Early Startups Should Target Category Killer Logos Over Volume
“So for me, the entire orientation of an organization in the early, early stages, I'm talking like sub a hundred. Now I think needs to be figure out the industries and the verticals. You can be successful and go get brand names, category killers and rotate hard…”
Shurtz: Tech companies eliminating CS still execute customer success functions
“You kind of need to go unpack titles versus roles, I think, and some of the companies that say, we don't need customer success. Someone Is playing that role and call them whatever you want.”
Shurtz: Pure sales farming does not exist in cloud software
“I actually kind of don't, I don't think that farming is a thing and in the cloud world, it's just not, I mean, you're responsible for finding new use cases across the entire bag that you have to sell.”
Shurtz: True sales verticalization requires specialization across all customer-facing roles
“To truly verticalize and to truly deliver value for customers, it can't just be the AE. It has to be, this was journey we went on. It has to be every single person that touches the account.”
Shurtz: Founders should focus on one industry vertical at a time
“If I was advising you and you're thinking of building out a vertical I would pick where you think the biggest bang for your dollars. And I'd try, I wouldn't go do three.”
Shurtz: Genesys requires close to $100M contract value for dedicated account coverage
“If I thought about Genesis, you would need to be, you'd probably need to be close to a nine digit customer.”
Shurtz: Genesys cloud product generates $1.4B in revenue
“But Jenna's also, you know, multi-billion dollar company, a cloud product that's 1.4 billion.”
Larry Shurtz: Discount Requests Without Documented ROI Mean Sales Reps Failed
“When someone asks for a discount, if it's my team that's asking me for a discount, I want to see the value proposition. I want to see the business case. If we don't have a business case, if we haven't articulated when they're going to get their money back, wha…”
Larry Shurtz: Blaming low sales on reduced customer spending is a mindset problem
“But I would be really, I would really push back on A leader or an AE that barring force majeure or some macroeconomic pandemic or a financial crisis, if you're selling to the banks, I would really push back any time today of someone saying, you know what? Peop…”
Larry Shurtz: Top sales reps leave because of bad leadership, not compensation
“When quality people start leaving, is comp an issue? Sure, yeah, I mean, comp, comp is likely always an issue. I don't think comp is always the issue, and I'm prioritizing the issues. And then it comes down to your leader.”
Shurtz: The FAB (Feature, Advantage, Benefit) sales strategy is dead
“Fab selling is pretty dead. FAB. Do you remember this one? Feature. Feature. Feature, advantage, benefit. This was a big deal. This was actually how I learned. And this was when I said, Eli Lilly, that was the training. So you were trained feature, advantage, …”
Shurtz: Cloud companies without a land, expand, and retain strategy will lose
“I think that, you know, in the cloud world, you have to be in a land and expand and retain sales strategy. And that's not just sales. That's customer life cycle. If you're not in that business, I think you're going to lose.”