Why Every Revenue Leader Needs to Understand Venture Capital (And Other Hard Truths)

My appearance on the Collin Cadmus Podcast

Podcast note: this week’s episode of TRLP will drop tomorrow (hopefully) and it’s a great one. I filmed with Adam Alfano (EVP, Global SMB & Emerging Products - Salesforce) at SalesForce World Tour earlier this week and we covered a lot. It was my first in person recording and there was a bit of production complexity hence the delay. Appreciate your patience!

I recently joined Colin Cadmus on his podcast to discuss everything from the "death" of outbound sales to why VP Sales tenure is so low. Colin started his career selling to restaurants at SinglePlatform, so we had an immediate kinship because anyone who's tried to get a pizza shop owner on a Google Meet while they're stirring marinara sauce knows it's a special kind of challenge.

What emerged was a conversation that went much deeper than typical sales tactics. We discussed fundamental shifts in how revenue leaders need to think about their careers, their companies, and the ecosystem we operate within. I also pushed back against some of his LinkedIn narrative that VPs of Sales are the victim of big bad meanie Founders and Venture Capitalists. 😆

Here are the six insights from the conversation:

1. Outbound Isn't Broken. It's Just Noisier

The conventional wisdom says email is dead, cold calling doesn't work, and traditional outbound is broken. This binary thinking misses the real issue.

The reality: Outbound channels aren't broken but they're certainly getting saturated. Every year brings more startups, more salespeople, and more noise competing for the same prospects' attention. Reply rates aren't declining because email stopped working (although deliverability is certainly down); they're declining because your prospects are drowning in mediocre outreach.

The solution: Raise your bar dramatically. At Owner, we've moved away from manual email personalization for our BDR team entirely. Instead, we’re centralizing outbound email and using AI to create hyper-personalized emails at scale, delivering genuine business insights our restaurant owner prospects didn't know about their own operations through in-house built tools like our AI Website Grader. Our BDRs then call with problem-based hypotheses tied directly to those insights.

The phone, meanwhile, is more effective than ever because so many sellers abandoned it for keyboard warrior sales using email and social. While everyone else chases the latest LinkedIn hack, we're booking 70-80% of our outbound meetings because we actually pick up the phone.

Framework: The Three-Channel Convergence

• Automated Intelligence: AI-driven emails that teach, don't pitch

• Human Connection: Phone calls with researched hypotheses

• Digital Coordination: Technology that serves insights to reps, not busy work

2. You Must Understand Venture Capital to Succeed as a Revenue Leader

This might be the most important insight from our conversation, and it's something I wish I'd learned 10 years earlier in my career.

Most revenue leaders operate with a massive blind spot: they don't understand the financial ecosystem they're swimming in. Whether you know it or not, your VC's fund construction, portfolio strategy, and return expectations determine a lot about how you need to operate.

The Power Law Reality: VCs invest in 50 companies expecting half to go to zero and maybe one or two to return multiple times their entire fund. This isn't pessimism, it's the math that powers the entire asset class. To return a $100M Seed fund (which would be a small emerging fund), you need outcomes worth $2B+ (assuming 5-10% ownership after dilution).

What this means for you: If you raised at a $50M Series A valuation, incremental improvements won't cut it. A 2x outcome ($100M exit) is essentially worthless to your investors, which most leaders don’t realize. They need you to swing for a massive outcome or strike out trying. Or else you’re not playing the venture capital game.

The Career Implications: Understanding this explains why founders make seemingly irrational decisions about spending and growth. It's not necessarily that they're bad operators (although there is plenty of that), they're just playing a game with rules that you might not fully appreciate.

Action Step: Read Sebastian Mallaby's "The Power Law" and start listening to 20VC. Your ability to influence strategy and make career decisions improves dramatically when you understand the financial forces driving your company.

3. VP Sales Tenure Is Low Because We Make Bad Choices

The average VP Sales tenure of 18 months and despite what you might hear from the whiners on LinkedIn, that isn't just a founder problem. In my humble opinion, it’s just as much a VP Sales/CRO problem. Extreme ownership y’all.

I see the same pattern repeatedly: talented first-line managers push aggressively for VP titles at mediocre companies instead of taking Director roles at exceptional companies. They optimize for title and comp over company quality, then act surprised when they get "scapegoated" for bad product-market fit.

The Uncomfortable Truth: In most cases where a VP Sales gets blamed for a bad product, they chose to join a company with a bad product. They did insufficient diligence, didn't talk to customers, didn't review the financials, and didn't stress-test the unit economics.

My Experience: I turned down my first CRO offer in 2019 to take a "Senior Lead" title at Shopify, which seems weird on paper if you’re chasing titles. Three years later, I took an SVP Sales title at Owner instead of other CRO opportunities because I optimized for company quality over title.

The Pattern: The companies most eager to give you the best title are often times the worst companies for your career. Great companies have negotiating leverage and they can attract talent without inflated titles.

Framework: The Company Quality Matrix

• Financials: Ask for a CFO walkthrough of growth model, retention, and unit economics. Go deep on business health.

• References: Back-channel aggressively with current and former employees

• Product Truth: Talk to actual customers, not cherry-picked references

• Market Reality: Understand competitive dynamics and total addressable market

4. Congruence Beats Optimization Every Time

One of the biggest mistakes I see in go-to-market strategy is trying to optimize multiple approaches simultaneously instead of choosing one and executing it exceptionally well.

At Owner, we made a clear choice: we're 100% digital. We don't do site visits, don't geo-target our sales team, and don't compromise our digital-first approach even when prospects request in-person demos. Meanwhile, Toast takes the opposite approach with regional reps, in-market support, and extensive field sales. Both strategies are working really well because they're congruent. I see other competitors trying to copy some of our approach and some of Toast’s then act confused when the results are poor.

The Trap: Many companies get stuck in the worst of many worlds by trying to be both digital and field-based, or attempting to serve both enterprise and SMB markets, or price premium and act discount with the same resources.

The Principle: Every decision should reinforce your core strategy. If you choose digital-first, every process, tool, and expectation should support that choice. Half-measures create confusion and mediocrity.

5. Radically Transparent Selling: A Methodology

Most sales methodologies focus on overcoming objections and closing techniques. I've built something different; a systematic approach to selling through radical transparency that builds trust faster and closes higher-quality deals.

The Core Principle: Lead with both your strengths AND your weaknesses to let buyers self-select in or out of the process early. This flies in the face of traditional sales wisdom, but it's devastatingly effective in today's trust-scarce environment. This is built off the principle of Psychological Reactance: when prospects feel pressured or that their freedom of choice is threatened, they automatically resist. This explains why traditional high-pressure sales tactics backfire, especially in today's market where buyers are already overwhelmed and defensive.

The restaurant business taught me that you can't fake authenticity; customers smell BS from a mile away, especially when they're getting pitched by five other companies that week.

The Five Pillars of Radically Transparent Selling:

1. Weakness-First Positioning Instead of leading with benefits, start conversations by acknowledging your limitations. "Before we dive into how Owner might help, let me be clear about who we're NOT a good fit for..." This immediately differentiates you from every other vendor who claims to be perfect for everyone.

2. Process Transparency Show prospects exactly how you work, including your challenges. "Our onboarding typically takes 2-3 weeks, and I'll be honest—the first week can be frustrating as we migrate your data. Here's exactly what that looks like..." Uncertainty breeds anxiety; clarity builds confidence.

3. Competitive Honesty When prospects ask about competitors, acknowledge their strengths honestly. "Toast has better hardware integration than we do, and if that's your primary concern, you should probably go with them. Here's where we excel instead..." This builds massive credibility and positions you as a trusted advisor, not a salesperson.

4. Outcome Uncertainty Never guarantee results you can't control. "Most restaurants see a 15-20% increase in direct orders within 90 days, but your results depend on factors like your marketing consistency and menu pricing. Let's talk about what would need to be true for you to see those results..." This sets realistic expectations and creates shared accountability.

5. Easy Exit Strategy Make it simple for prospects to say no or leave later. "We don't do long-term contracts because I believe if we're not earning your business every month, we shouldn't have it. You can cancel anytime with 30 days' notice, and I'll personally help with the transition." This removes pressure and paradoxically increases commitment.

The Psychological Foundation: This methodology works because it triggers three powerful psychological responses:

• Reciprocity: Vulnerability creates obligation to reciprocate with honesty

• Authority: Acknowledging limitations demonstrates expertise and confidence

• Consistency: When prospects choose you despite knowing your flaws, they're more committed to making it work

The Business Impact: This approach has made us the highest-rated restaurant technology company across all categories. We have the best ratings and reviews of any company in restaurant software because we attract buyers who are genuinely aligned with our solution and we work with them in an honest and transparent fasion.

The Career Impact: Revenue leaders who master this methodology become trusted strategic partners rather than vendor managers. You'll get invited to bigger conversations, receive more referrals, and build a reputation that follows you throughout your career.

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Additional Considerations

Further learning:

• "The Power Law" by Sebastian Mallaby

• "Thinking in Bets" by Annie Duke

• "The Five Dysfunctions of a Team" by Patrick Lencioni

• Start listening to venture capital podcasts (20VC, BG2, Uncapped, Topline, a16z)

Tools to Explore:

• Momentum.io for automated sales intelligence

• Clay for data enrichment and personalization

• Jordan Crawford's cold email frameworks