Topline · 23 Aug 2026 · From the week of 17 August
The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Rick Smolen, CRO of ShipHero and sales advisor to Riverwood Capital's portfolio of enterprise software companies, joins hosts Sam Jacobs, AJ Bruno and Asad Zaman to discuss AI in go-to-market and revenue leadership. The conversation covers AI as leverage rather than a shortcut, why AI note-takers and automated follow-ups can weaken enterprise selling, and why ShipHero has not raised quotas despite AI investment. Rick also shares a scorecard for judging revenue leaders beyond the number, and the episode touches on getting fired and a bull case for HubSpot. The central argument is that AI amplifies both strong and weak sellers, and that the human judgment and nuance of enterprise selling cannot be outsourced.
For founders
- Rick expects AI to make the best sellers much better while making the weakest sellers easy to spot.
- Rick says ShipHero has not raised quotas on anyone despite meaningful AI investment, and he does not think doubling an enterprise quota would give a rep any chance to succeed.
- Rick warns that outsourcing note-taking to AI tools removes the tone and nuance that matter in enterprise deals.
- Rick says ShipHero vibe-coded its demo and a tool called Sales Hub, so demos are set up and personalized much faster. He says this works because a demo is customer-facing but not used by the customer, so it does not need the rigor of the core product.
For revenue leaders
- Rick says ShipHero tracks whether qualified-opportunity-to-close conversion is improving and whether reps are qualifying more deals, and reports meaningful conversion gains in 2026 that he credits to the tools the company gave sellers.
- Rick says ShipHero no longer runs paid search and is spending on visibility in LLMs, a channel where he says no one knows the exact answer yet.
- Rick says a sales leader or CRO should be judged on team quality, operating rhythm and the quality of their plan, not on business performance alone.
- Asad says enterprise sellers are constrained by travel and meeting capacity, so he does not expect their quotas to grow several times over, though they may need somewhat more pipeline in a competitive market.
What was said 24, most useful first
AI-native companies including OpenAI, Cursor, Factory and Anthropic have hired classic enterprise CROs to build their go-to-market teams. Listen
Asad lists recent CRO hires at these companies and notes that several have roots in classic enterprise sales, including a lineage tied to John McMahon. He says these teams look much like the leading sales teams of the previous generation, after a period a year or two earlier when people expected sales to look completely different with no quotas. He draws the conclusion that the pattern has returned to hiring disciples of McMahon to run the market.
“we're back to like, let's just hire John McMahon's disciples and let them run at the market.”
Listen to the episode Sales team, hiring & comp Link to this
Reported rep productivity gains at hot AI companies come from a demand surge that cannot be counted as a general benchmark. Listen
Asad notes the claim that reps at some AI companies are performing at two to four times prior quotas. He says a gold rush, where buyers are throwing money at a market, produces word-of-mouth demand that cannot be counted as a repeatable result. He does not think enterprise sellers who travel and meet in person can do three or four times their quotas once the market settles.
“I don't think that there's a lot of reason to believe that people that have to travel to see customers and do dinners and do conferences can do three, four times their quotas.”
Listen to the episode Sales team, hiring & comp Link to this
ShipHero has moved its marketing budget away from paid search and is testing ways to appear in LLM answers, though no one knows the exact method yet. Listen
Rick says the budget movement is from Google paid ads toward showing up in LLMs, sometimes called AEO or GEO. He says everyone is experimenting because no one knows the answer for certain. He says ShipHero no longer does paid search at all, and that the company is spending on experimentation in this area.
“We don't even do paid search anymore at all.”
Listen to the episode Pipeline & demand generation Link to this
ShipHero built a vibe-coded customer-facing demo tool that it says makes demos faster to set up and better fitted to each prospect's flow. Listen
Rick says ShipHero built a tool it calls Sales Hub, which lets the team personalize demos much faster and fit each prospect's flow. He argues a demo tool like this does not need the rigor of the core product because it is customer-facing but not used by customers, and the audience is a captive one that understands the workarounds. He calls it one of the best achievements he has seen the team deliver.
“we've like vibe coded the demo and something we call Sales Hub.”
Rick suggests building customer-specific applications alongside the core product so a company can say yes to edge-case requirements, with forward-deployed engineering teams as a way to do it. Listen
Rick says a core offering may handle around 90% of what customers need, and that the remaining edge cases can be handled by building applications that complement the core product. He says this is more possible now, but that it adds complexity because forward-deployed engineering teams must work with core engineering. He says each organization should decide which things it will not build into the core product but will still say yes to.
“what are the things that we're not going to build into our core offering? But we should be able to say yes to”
A sales leader or CRO should not be measured solely on business performance, because strong products can succeed without a good leader. Listen
Rick says he has seen bad CROs at great products and companies that were growing rapidly regardless of who led sales. He says business performance is an indicator but not the indicator. He points to team quality, operating rhythm and the plan the leader has for the next stage as things that matter in judging performance.
“I don't believe a sales leader or a CRO should be measured solely on business performance”
Rick predicts AI will make the best sellers about 10x better, while weaker sellers fall further behind and become easy to see. Listen
Rick says the spread between top and bottom performers will widen rather than lift everyone equally. He says the best sellers will use AI to prep, target better customers and follow up more efficiently, while those who expect AI to do the work for them will be unmistakable. This is his prediction, based on what he says he is observing.
“I do believe that the best will become 10x better.”
AI note-takers capture objective events but miss tone, nuance and emotion, so sellers who rely on them may perform worse. Listen
Rick argues that a seller's notes are where they process what happened and decide the next action, and that an AI note-taker captures much of the objective content but not the buyer's reactions. He cited an old study he could not detail, in which computer-scored tests gave results without the context teachers had when grading by hand. He warns that a seller who treats note-taking as saved time may see performance decline.
“the computer can't capture the tone, can't capture the nuance, can't capture the content”
Much of the valuable work in sales happens between meetings, and he thinks having sellers on calls 85% of the time is too much. Listen
Rick says sellers need time after a call to think through next steps and strategy. He says he does not agree with a target of putting sellers on the phone with customers 85% of the time. He frames this as a reason sellers should not hand note-taking or processing entirely to a tool.
“the magic in sales is often happening between the meetings”
ShipHero has not raised quotas for any of its reps, even though AI has helped the team. Listen
Rick says quotas were already high at ShipHero and the company has a rationale for the OTE-to-quota multiple. The company has expanded the team and allocated more quota across it rather than raising individual quotas. Rick says he does not believe doubling someone's quota would give them any chance to succeed, because the selling variables AI has not changed still apply.
“We have not raised quotas on anybody on the team.”
Listen to the episode Sales team, hiring & comp Link to this
Asad doubts enterprise sellers can carry quotas several times higher than today, because travel and meeting capacity limit them, though pipeline needs may rise. Listen
Asad says enterprise sellers who travel, meet people in person and attend dinners and conferences have a limited number of hours. He expects their quotas will not grow much, but says that in a more competitive market, where win rates are going down, they may need somewhat more pipeline to hit the same numbers, though not multiples of what they had before.
“I don't think their quotas grow up that much, but they might need a little bit more pipeline than before”
Listen to the episode Sales team, hiring & comp Link to this
Rick measures sales capacity by how many leads one person can reasonably handle in a month, given the sales cycle and the expected conversion rate. Listen
Rick says the framework depends on the sales cycle. In enterprise, he says the constraint is travel and meetings, so a seller may handle only a limited number of demos. He then considers expected conversion rate, deal value and time period, and says he is open to higher productivity if the logic supports it.
“how many leads can a person reasonably handle in a month?”
Listen to the episode Sales team, hiring & comp Link to this
Enterprise and mid-market selling depends on a soft side, where the seller works out what each buyer is trying to achieve, such as a promotion, and how to help them get it. Listen
The speaker says buyers often purchase the product plus a personal or political outcome, so sellers must catch nuance about what each stakeholder is solving for, who their boss is and how decisions get relayed. He argues this requires a human who is looking for that nuance, and that commentators who have not sold this way may misjudge the future.
“the soft part of sales which is where the enterprise seller or the mid-market seller has to catch the nuance”
The winning seller now diagnoses a customer's problem better than the buyer can, rather than relying on product expertise. Listen
Rick contrasts the past, when product expertise won because information was scarce and product knowledge had to be installed and taught by the vendor, with today, when information is everywhere and switching costs are low. He says sellers now need industry expertise, knowledge of where CFOs will spend, and alignment to customer outcomes. He says the methodology used by leaders such as John McMahon is about creating customer value by uncovering problems worth solving.
“the winner is in somebody that can actually diagnose the problem better than the actual buyer can do it themselves.”
ShipHero watches whether conversion rates are improving and whether reps are using tools that help them win more deals, noting that CEOs can now check these numbers themselves. Listen
Rick says CEOs can connect their systems to AI tools and pull conversion rates from HubSpot, so a CRO has less room to present numbers unchallenged. He says transparency is good when the numbers are accurate. The two measures ShipHero focuses on are whether conversion rates are improving and whether the team is using tools that help it win more deals, such as being able to say yes to more requirements.
“So one of the things we're looking at is like, hey, is the conversion rate improving?”
ShipHero has seen meaningful improvement in conversion from qualified opportunity to closed deal, and he credits it not just to better sales language but to the company equipping sellers to win more deals. Listen
Rick says ShipHero invested in AI in 2026 and that it has helped go-to-market. He gives no figures, but says the improvement is in the conversion rate from a qualified opportunity to a closed deal. He says he does not believe the gain comes only from sellers saying better words, and that sellers have been equipped by the company's capabilities to win more deals.
“Meaningful improvements in conversion rate from a qualified opportunity to close one.”
AI tools such as Claude and Clay let marketers build lead lists and ICP targeting better, faster and deeper, and layer in intent and signals on ABM. Listen
Rick says he can build lead lists, identify ideal customer profiles and find contacts more quickly with these tools, which he calls a cheat code for this part of the work. He says ABM has not gone away but should be more effective because it can layer in intent and signal data. He expects better outbound and event attendance because the team is reaching the right people.
“I can build lead lists better, faster, deeper than ever before.”
Listen to the episode Pipeline & demand generation Link to this
He piloted AI role-play about a year ago but did not find it authentic enough, so he has not adopted it for his team. Listen
Rick says he is a supporter of AI role-play for practice and ramping new hires, and he compares it to athletes practicing before games. In his initial pilot the tool did not feel authentic enough for sellers to take it seriously, and he judged that adoption on his team would be low. He says the tool landscape may have improved since then.
“it didn't feel authentic enough in my initial piloting of it that I thought that like Somebody would take it seriously”
Listen to the episode Sales team, hiring & comp Link to this
A revenue leader's most important job is building the team, and he calls team quality 80% of the game. Listen
Rick says the leader must judge whether they have the right people for the company's stage, such as zero to one, product-market fit or scaling. He says it is easy to rationalize mediocre performance and that great leaders keep upskilling the team, holding a high bar and attracting the right talent. He treats this as the first of several variables for judging his own leadership.
“the quality of the team that you build, the quality of the team that you manage is 80 % of the game.”
Rick evaluates his leadership through an operating rhythm that balances team motivation, engagement and accountability, using rituals, meetings and clear expectations. Listen
Rick says he asks whether the team is motivated, engaged and accountable. He notes that motivating people and holding them accountable can pull against each other. He says the skill is building a set of rituals, meetings and expectations that gives clarity, high motivation and a high bar, so that a sales team does not run over its leader.
“is the team motivated? Are they engaged? And is there accountability?”
Sellers should make the most of strong markets and reframe their motivation when markets are weak. Listen
Rick says ShipHero used its sales kickoff theme of catching the wave to encourage the team to capitalize on a growing market, because downturns will come. He wants younger team members to understand that conditions will not always be this easy. In weak markets he says the revenue team's job is to play the best hand possible, which can include changing bonuses or using spiffs to motivate people in other ways.
“Make the hay while you can.”
AI is leverage, and it can either greatly improve or badly damage sales performance depending on how it is used. Listen
Rick compares AI to debt, which amplifies results in either direction. He says AI is not good or bad in itself; what individuals and teams do with it determines the outcome. He describes using AI as a partner that helps a seller prepare, target and follow up, while the seller still owns the work.
“It's like debt. Like debt is leverage. It can make performance exceptionally good or it can bankrupt you.”
AI can be a thought partner for writing, but the person sending the content must own it and stand behind it. Listen
Rick says it is fine to draft an email with AI and then ask it to add more empathy, since he describes himself as naturally a bit of a jerk. He stresses that the message is still from the person who sends it and must be defensible. He sees AI as useful for copy in a thought partnership role, not as a substitute for the person's own work.
“I think that these things can be a thought partner, but you have to own your content.”
A CRO should hold themselves accountable to a clear plan rather than excuses, and that departures are not always caused by the plan. Listen
Rick says a leader should have a plan that is bold or incremental and that they can stand behind, with no shortcuts in the work. He says that when a plan is solid and the work is sound, the leader should feel good about it regardless of outcome. He adds that how a leader is judged by a board or CEO may depend on other factors, so he advises against worrying too much about politics.
“You should have a plan and not excuses.”