From 1-Hour Interview to Actionable Insights in Minutes.

[00:53] Mark O'Connell: The main challenge is stagnation. That's the word for it. For three years, we were on a rocket ship. We were growing 150% year-over-year. The sales team was hitting their numbers, the champagne was flowing. It felt easy. Then, about a year ago, we made a strategic decision to move upmarket... And that’s when we hit a brick wall. Our growth has flattened to maybe 10% year-over-year, and my forecast for the next two quarters is looking even softer.

[02:02] Mark O'Connell: It was a velocity game. Pure and simple. We had a great inbound engine, thanks to marketing. An SDR would qualify them in a 15-minute call, and an Account Executive, an AE, would have the deal closed within 30 to 45 days. The average contract value, or ACV, was around $25,000. It was transactional.

[02:47] Mark O'Connell: It's a different universe. The ACV isn't $25k, it's $250k, maybe even half a million. The sales cycle isn't 30 days, it's 9 to 12 months. You're not talking to a single IT manager; you're navigating a buying committee of six to ten people across legal, finance, security, and multiple business units. It's a complex, multi-threaded sale that requires a consultative approach.

[03:45] Mark O'Connell: It’s a mess, Sarah. It’s a complete mess. Our inbound-heavy model doesn't work for landing a company like Johnson & Johnson. We've tried to bolt on an outbound, Account-Based Marketing—or ABM—strategy, but it feels... amateurish. We bought all the expensive tools, we have Outreach for sequencing, we use LinkedIn Sales Navigator, but the team is just throwing spaghetti at the wall. The messaging is generic. The SDRs are sending the same email to a VP at a Fortune 500 company that they'd send to a startup. The conversion from a cold outreach to a qualified first meeting is abysmal. I think it's under 1%.

[04:42] Mark O'Connell: All of the above. We don't have a defined Ideal Customer Profile, an ICP, for the enterprise segment. So the SDRs don't know who to target. We don't have a real sales playbook for outbound, so they don't know what to say. There's no value proposition tailored to a Chief Financial Officer versus a Chief Technology Officer. It's spray and pray, and it's burning through our budget and our reputation.

[05:27] Mark O'Connell: The handoff is another point of failure. It happens in Salesforce, and frankly, our Salesforce instance is a disaster zone. There are no standardized fields for the information an AE needs. The notes from the SDR are often just a couple of cryptic sentences. So the AE goes into that first major call with a potential six-figure client effectively blind.

[06:12] Mark O'Connell: Oh, where to begin. It was set up five years ago for the high-velocity, simple sales model. It's never been overhauled. We have duplicate records everywhere. Data is incomplete. AEs don't update it consistently because it's so clunky. They all have their own "shadow CRMs" in spreadsheets or personal notes. As a result, I have zero visibility into the pipeline. I can't generate a reliable forecast to save my life. For a company called 'DataWeave Analytics,' it’s incredibly ironic that our own sales data is a black box. We're flying blind, trying to land a 747 with the instruments from a Cessna.

[07:23] Mark O'Connell: No. That's the other big gap. We have no standardized sales methodology. Some of my reps who came from other companies try to use what they know... you hear them mention MEDDIC or Challenger Sale, but there's no formal adoption, no training, no reinforcement. So every single AE is running their deals differently. There's no common language for deal reviews. There's no checklist for what constitutes a "qualified" opportunity at Stage 3 versus Stage 4. It's all gut feel. This leads to massive pipeline inflation.

[08:18] Mark O'Connell: It's crushing them. My top performers from the mid-market days are struggling the most... I've had two of my best reps leave in the last six months for jobs at companies that have a more transactional model. The team's morale is low. They feel like they're being set up to fail, and frankly, I don't blame them.

[09:03] Mark O'Connell: It's wide. They're great at demoing the product... But they're not business consultants. They don't know how to read a balance sheet or have a conversation with a VP of Finance about Total Cost of Ownership. They don't know how to build a champion internally. They don't know how to navigate competitive bake-offs.

[10:04] Mark O'Connell: It's almost always SynthCorp. They're our boogeyman... Their product isn't even as good as ours!... But they win the deals. Their go-to-market is just... slicker. Their salespeople are polished. They have an army of sales engineers and value consultants... We show up with a standard demo. It's like we're bringing a knife to a gunfight.

[11:05] Mark O'Connell: So the challenge isn't the product, it's the entire commercial wrapper around the product—the sales process, the methodology, the team's skills, and the competitive strategy.

[11:15] Mark O'Connell: My engineers and product guys don't always get it. They say, "But our product is better!" and I say, "It doesn't matter if we can't get it in front of the right people with the right message and shepherd the deal to a close." A great product with a C-grade sales process will lose to a B-grade product with an A-grade sales process every single time. And right now, we're operating with a D-grade process.

[12:02] Mark O'Connell: I wish I could track everything. Right now, I can track activity metrics—number of calls, number of emails sent. Useless, vanity metrics. What I need is performance metrics. I need to see my lead-to-opportunity conversion rate by source. I need to see my pipeline velocity—how long deals are sitting in each stage. I need to know my Customer Acquisition Cost—CAC—for an enterprise customer... I need to know our win-rate against competitors like SynthCorp. I can't see any of this reliably. I'm making multi-million dollar decisions based on anecdotes and gut feel.

[14:14] Mark O'Connell: Onboarding is a two-week program focused almost entirely on product knowledge. A new hire can tell you about every API endpoint we have, but they can't tell you the top three business pains of a Chief Marketing Officer. We have no ongoing training. No reinforcement. We did a one-day "consultative selling" workshop last year, and it was a complete waste of money... because there was no follow-up, no change in management, no coaching from the frontline managers to support it. Our managers are glorified deal-chasers. They're not coaches, because they were our best AEs from the old model.

[15:12] Mark O'Connell: A hundred percent. We promoted our best players to be coaches, without ever teaching them how to coach. It's the classic mistake.

[15:37] Mark O'Connell: That's a fair question. Our biggest asset, without a doubt, is the product. It truly is excellent and our customers who use it, love it. Our Net Promoter Score is over 60, which is world-class for B2B SaaS. Second, I do have a core group of people on the team who are hungry. They're frustrated, yes, but they're smart and they want to win. And third... well, we have the budget to fix this. The board is committed to the enterprise strategy; they know it's not a simple switch.

[16:38] Sarah Jenkins: That's the perfect place to end for today. A great product, a motivated core team, and executive support. Those are powerful building blocks. You've given me a phenomenal amount of information to work with. My next steps will be to synthesize this and combine it with the interviews I'm having with your marketing and customer success counterparts. We'll start to form some initial hypotheses on the highest-priority workstreams, which we'll then validate with you and the rest of the leadership team in a couple of weeks.

[17:08] Mark O'Connell: That sounds great, Sarah. I'm looking forward to it. And really, thanks for listening. It was actually therapeutic to just lay it all out like that.

[17:18] Sarah Jenkins: That's what I'm here for. I'll be in touch to schedule our next checkpoint. Have a great rest of your day.

[17:24] Mark O'Connell: You too.