Nov 10, 2023 · 57m · news
Chris Degnan: Why You Should Hire a Head of Sales Sooner Than You Think | E1080 · 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 Chris Degnan, Chief Revenue Officer at Snowflake, who shares tactical insights on scaling sales organizations, defining product-market fit, and the operational discipline required to grow product revenues from zero to over a billion dollars.
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 31.2% of the talking time here. How this is scored →
Harry as informed peer 2.9 Guest teaching 5.1 Guest disagreement 3.1 Harry pushing back 2.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 46:53 Customer Success is a Naughty Word
Chris aggressively rejects standard SaaS playbooks by labeling Customer Success a naughty word and explicitly telling founders to fire their CS teams in favor of technical SEs and billable professional services.
Hardest push from Harry ▶ 48:36 Pushing Back on Eliminating Customer SuccessHarry refuses to accept Chris's dismissal of Customer Success orgs, pushing back on how account monitoring and renewals can be sustained if reps are forced to manage both growth and retention quotas alone.
Biggest teaching moment ▶ 31:37 Product Marketing is a Waste for Early StartupsChris educates Harry and listening founders on early go-to-market mistakes, arguing that hiring product marketers for collateral creation is a waste of capital compared to hiring pipeline generation marketers.
Harry holds his own ▶ 12:56 Challenging Category Creation vs Customer EducationHarry uses venture strategy expertise to challenge Chris's preference for existing demand, asking whether avoiding customer education forfeits category creation opportunity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Entry into Sales & What Drives Competition | 2 | 3 | 2 | 1 | Harry asks about Chris's entry into sales and compares sales deal-closing highs to venture capital return timelines. Chris offers a slight reframe, noting that closing a deal provides immediate gratification, but every new quarter resets the bar and makes you feel like a loser again. | |
| The Journey to Snowflake | 3 | 4 | 1 | 1 | Harry highlights investor Mike Speiser as an under-the-radar gem, showing familiarity with top Silicon Valley venture operators. Chris details taking a huge cash pay cut to join zero-revenue Snowflake as employee number 13 based on founder quality and market size. | |
| Defining the Sales Playbook & Identifying the ICP | 4 | 6 | 3 | 4 | Chris outlines his core rule of completing eight sales calls per week and finding ICPs by targeting existing cloud-native Redshift users. Harry pushes back on avoiding customer education, asking if that dynamic sacrifices category creation. Chris reframes the point, arguing that trying to educate buyers creates unsustainable 18-to-24-month sales cycles. | |
| Timing the Head of Sales & the First Hire | 4 | 5 | 2 | 3 | Harry asserts a firm rule that founders should never hire a head of sales until they have a fully defined sales playbook. Chris adds nuance, noting that founders must possess humility and adapt based on customer feedback, sharing how he started as sales director with the assumption he might be replaced as the company scaled. | |
| Accountability & the Sales-to-Product Feedback Loop | 2 | 5 | 2 | 2 | Chris explains how he held himself accountable early on by sending weekly summaries of all eight sales calls directly to engineers and board members. He details acting as a bridge to product teams, giving the example of bringing technical feedback on feature gaps like windowing straight to founders. | |
| Motivation, Forecasting, & Urgency in Enterprise Deals | 2 | 5 | 3 | 2 | Harry asks how sales leaders can create urgency and forecast effectively. Chris dispels sales reps' romanticism about client relationships, bluntly stating customers care about their own jobs and families, so reps must identify concrete compelling events and hard ROI. | |
| Sucking the Life Out of Startups & Multi-Threading Champions | 3 | 6 | 3 | 3 | Chris warns startups that large enterprise clients will suck the life out of early companies by demanding a hundred custom features before abandoning the project. He also shares how Frank Slootman called him a deal jockey and demanded he build leadership scale rather than personally managing every transaction. | |
| Building Sales Teams & Marketing's Pipeline Mission | 3 | 6 | 4 | 4 | Chris argues strongly against early startups hiring product marketers to produce literature, calling it a waste of time compared to hiring pipeline generation marketers. Harry challenges how to measure pipeline marketing without reps gaming soft metrics, leading Chris to explain focusing strictly on qualified meetings. | |
| Outbound Prospecting, Churn, and CFO Spending Trends | 3 | 6 | 5 | 3 | Chris rejects claims that cold calling and outbound prospecting are dead, calling proponents of that view crazy. He also dismisses assertions that CFO spending is frozen, calling BS and explaining that CFOs continue spending on core value products while cutting nice-to-have tools. | |
| Developing Talent & Identifying Failure | 2 | 5 | 4 | 3 | Harry questions whether sales reps should feel safe in their roles. Chris strongly pushes back, insisting reps require constant pressure and admitting he never feels safe himself, quoting Frank Slootman's motto that when there is doubt, there is no doubt. | |
| Hiring in Pairs & Radical Directness | 3 | 5 | 3 | 3 | Harry suggests hiring reps in pairs to isolate territory quality from rep execution. Chris agrees and shares Frank Slootman's stark reality of corporate life that board members and colleagues are not your friends, reminding sales leaders of their primary duty to shareholders. | |
| Scaling CRO Roles & Managing Board Expectations | 3 | 5 | 2 | 3 | Harry asks if sales executives can scale across all growth stages or if founders fire heads of sales too quickly. Chris explains that board advisors like John McMahon provided blunt feedback that enabled his personal scaling, while emphasizing that diagnosing bad quarters requires objective metric analysis rather than emotion. | |
| Customer Success is a Naughty Word | 4 | 7 | 7 | 5 | Chris delivers his strongest contrarian stance, declaring Customer Success a naughty word and advising founders to eliminate CS teams in favor of technical sales engineers and paid professional services. Harry pushes back forcefully, asking how companies avoid churn and manage renewals without dedicated CS reps. | |
| Rip the Bandaid Off & Quick Fire Round | 3 | 4 | 3 | 2 | Chris recounts resegmenting the sales force prior to IPO as a necessary bandaid-rip. In the quick-fire section, he declares wine-and-dine golf selling dead and praises Amazon's co-opetition strategy. |
Statements from this episode (25)
In business, no one is your friend; duty is to shareholders
“No one's really your friend. You have a job to do, and you have an obligation to shareholders.”
Sales success resets every quarter, making you a loser all over again
“The immediate gratification is, is definitely something that that I enjoy. But it's always like, it never ends, because once you have a good quarter, it's on to the next quarter, and you're a loser all over again, so.”
Snowflake had no website or CEO when Chris Degnan joined
“I was actually hired at the time. They didn't have a website. They didn't actually have a CEO at the time.”
Snowflake had zero customers when Chris Degnan joined, despite Netflix rumors
“There was some insinuation that Netflix was a customer. They were not. There was zero customers when I showed up.”
Mike Speiser barred Snowflake's first sales hire from selling for two years
“Mike Speiser was like, for two years, you're not selling a thing. Like, I don't want you to sell anything. I just want you to get customer feedback.”
Educating prospects on a problem creates an 18-to-24-month sales cycle
“The reality is, is that if you're out there trying to convince people that they have a problem, that's an 18 month to 24 month sales cycle.”
Mike Speiser hired Chris Degnan expecting to fire him within two years
“Mike Spicer didn't hire me to be the chief revenue officer of Snowflake. And in fact, I think he probably said to each of the board members, we'll probably fire Chris in a year or two. I was a director of sales.”
Founders should hire a VP of Sales before a Chief Revenue Officer
“I think it's a mistake for a founder to hire a chief revenue officer right away, because the getting rid of a chief revenue officer is going to be more painful versus, Hey, you have a VP of sales and you can hire over them and you can make that VP of sales a H…”
Snowflake co-founder built the initial windowing feature overnight after customer request
“And that night, the brilliance of Terry goes home and builds the basic concept of what is Selflake's windowing Functionality today.”
Degnan barred Snowflake sales reps from forecasting deals before product trials
“Early on, I actually wouldn't let the sales team put an opportunity in Salesforce to forecast it unless the customer had tried the product.”
Early enterprise sales drain startup resources through custom feature demands
“Those large enterprises, especially in an early stage startup, they will suck the life out of that startup because they will say, I need these hundred features.”
True enterprise sales champions willingly introduce reps to the economic buyer
“A good way to test that champion. If they are real champion is will they actually bring you to the economic buyer?”
Enterprise sales reps must direct executive involvement rather than surrender control
“A good sales rep uses us as a pawn. I always say, I'm an actor in the sales reps movie. They're the director. They can use me however they want. If they make me the director, good luck, and you're probably going to fail.”
Early startup product marketing literature is a complete waste of time
“Founders love product marketers. They understand the product and they're going to build this marketing literature and stuff like that. That's a waste of time. The marketing team needs to generate pipeline.”
Snowflake abandoned MQL and SQL metrics to focus solely on qualified meetings
“When we hired our CMO almost seven years ago, Denise, I was arguing with the previous marketing team over what a, you know, an MQL was when an SQL was and all this other stuff. And it was driving me crazy. And she said, great news. We're never going to talk ab…”
Outbound cold calling and prospecting are not dead in enterprise sales
“Prospecting should never die. Cold calling should never die. You got to find, find champions. The way you find champions is you're going to say, Hey, I heard you have this issue. Anyone who says that's dead is crazy.”
Consumption billing models provide real-time visibility into potential customer churn
“So with Snowflake being a consumption model, you could see the dial turn real time. I look at revenue on a daily basis. And if a customer goes up really fast or down really fast, it sets off alarm bells because I don't want them to overspend because all of a s…”
Sales reps fail without eight weekly calls and deep product knowledge
“If you do not go on eight sales calls a week, if you do not become a student of what you sell, you will fail. You might be a really nice person, but if you don't do those two things, you're going to fail.”
Fire sales reps who lack deep product knowledge after six months
“If you go out on a sales call, and the person doesn't know what the hell they're talking about, and they've been on the job for six months, yeah, you're going to be in a world of hurt, and you should just cut bait.”
Sales leaders must hire reps in pairs to test territory viability
“A hundred percent. Like that's a good lesson is like, A single person should not be the litmus test because you don't know if they're doing the things that you do. As the sales leader, you should be a leading from the front sales leader. You should understand …”
Founders often unfairly blame sales leaders first for startup failures
“I think CEOs, founders like to blame other people for failures. Sales, sales is probably the first person to get the finger pointed at.”
Board complaints about sales usually reflect poor product-market fit
“I've seen that, you know, the board of directors is saying this person stinks and they don't. It's more that the founders aren't listening to customers. They're not building the right product.”
Founders should eliminate Customer Success and hire technical sales engineers
“Yes. Get rid of them. Build a professional service organization. Hire more SEs who can do it. Customer success. Look, people think that's blasphemy. I get it. I don't believe in it. I inherited our customer success when Frank came in and he gave it to me. I go…”
Snowflake operates professional services at low single-digit profit margins
“So our professional services organization is a single digit profit margin business. It is not something wall street cares about in terms of our services revenue. It's an enablement function. It remains profitable, but at a low margin. So we're not losing money…”
Amazon has the best sales strategy for co-existing with competitors
“Amazon, they invented the cloud. They invented how to work with companies like us. We were hard for them because we competed with a product of theirs or multiple products of theirs, but yet they make us successful. So it's a hard thing to do, but for them to b…”