Here’s the the reality every founder running sales, and every first time VP of Sales and sales leader learns the hard way:
You can’t coach someone into being something they fundamentally aren’t. Especially a sales exec.
I’ve seen this pattern play out literally 100+ times across B2B companies from Series A to IPO. Again and again and again. Founders and sales leaders keep making the same mistake—they hire for one motion, then expect their reps to magically transform into something completely different when growth demands it.
Let’s break down the three realities that will save you months of frustration and missed numbers.
The Inbound-to-Outbound Illusion
95% of sales reps who have only done inbound won’t start doing real outbound, even if they’re missing quota.
No matter what they say or claim, they just won’t.
I’m not talking about the performative outbound they’ll do when you’re watching. They’ll send a few LinkedIn messages, maybe fire off some templated emails, and call it a day. But the grind of true outbound prospecting? The 50+ calls per day, the real research, the rejection resilience?
Not happening for 95% of reps that have mainly worked in an inbound environment. They just don’t want to do it, or see it as a good use of their time.
Why? Because inbound reps have been conditioned to work leads that are already warm. They’ve never developed the muscle memory for cold outreach, and more importantly, they’ve never built the emotional fortitude for it. When you’ve spent years closing deals from demo requests, the leap to interrupting someone’s day with a cold call feels impossible.
Rippling’s CRO Matt Plank learned this lesson the hard way during their transformation from programmatic outbound to human-driven outbound. When they had programmatic sequences hitting thousands of accounts, they were getting 1% conversion rates. But when they built a team of 150 dedicated outbound SDRs and had them work those same accounts, conversion jumped to 3-7%.
Same accounts. Same market. The only difference? They hired people who were wired for outbound instead of trying to convert their existing team. As Matt puts it, 50% of Rippling’s demos are still booked over the phone—the old-fashioned way.
The Fix: Don’t try to convert them. If you need outbound, hire outbound specialists. Period.
The Feast-or-Famine Cycle
Here’s another pattern that’ll drive you crazy: 95% of sales reps who will actually do outbound stop once they have enough inbound leads to hit their comp goals.
This one burned me personally when we scaled from $2M to $10M ARR. Our best outbound rep suddenly went dark on prospecting the moment our content marketing kicked in and inbound volume spiked. His pipeline was full, quota was covered, so why keep dialing?
From his perspective, it made perfect sense. From a business growth perspective, it was a disaster. We needed consistent pipeline generation, not this feast-or-famine cycle where outbound efforts disappeared every time marketing had a good quarter.
Toast’s CRO Jonathan Vassil learned a similar lesson about incentive structures. He admits that getting the comp plan right to drive consistent behavior was “a complex process that required iteration and learning.” Even at Toast’s scale, they’re still fine-tuning incentives to prevent reps from coasting once they hit their numbers.
But here’s what Toast does differently: they foster a culture where reps strive to achieve 200% or 300% of their targets, not just 100%. They actively combat the tendency to slow down after reaching quota. The culture matters as much as the comp plan.
The Reality: Most reps optimize for their personal number, not your company’s long-term growth. You need comp plans and management systems that account for this.
The Field Sales Fantasy
Let’s talk about the elephant in the room: 95% of sales reps don’t really want to visit customers in person. Even many “enterprise” reps.
The pandemic didn’t create this trend—it just gave everyone permission to admit what was already true. Most sellers, even those selling $100K+ deals, will visit the fewest customers possible. They’ll find every reason why a Zoom call is “just as effective” as being there in person.
But here’s where the data gets interesting. Toast’s CRO Jonathan Vassil shared something that should make every sales leader pay attention: prospects who receive an on-site visit close at a 3X higher rate than those who don’t (45% vs 15% conversion).
And it’s not just Toast. Sam Blond, former CRO of Brex, tracked this rigorously in their CRM. If their average virtual conversion rate was 15-20%, in-person meetings pushed that to 45-60%. Christian Smith, CRO of Splunk, sees the same 3X conversion lift when his enterprise reps show up in person, even for complex multi-million dollar deals.
Think about that for a second. We’re not talking about a marginal improvement—we’re talking about tripling your close rate. Yet as Sam Blond points out, “most reps only want to meet in person for the big, halo deals. You may need different DNA if you want typical SaaS B2B reps to get out there in-person.”
There’s the rub. Even when the data is crystal clear, even when the ROI is undeniable, most reps will find every excuse to avoid that plane ticket. Toast employs a primarily field-based sales organization, with 75-80% of sales reps working in the field, but that means 20-25% still prefer to stay put.
And these are reps selling into restaurants—a notoriously relationship-driven industry where trust matters more than features. If Toast, with their incredible unit economics and billion-dollar success, can only get 75-80% of their team into the field, what does that tell you about the average SaaS company?
The Truth: If your deal size and sales cycle demand in-person relationship building, hire people who actually enjoy it. Don’t try to force office dwellers onto planes. The math works when you have the right people, but it only works with the right people.
What Most B2B Sellers Actually Want
Strip away all the job descriptions and sales training, and here’s what the majority of B2B sellers really want:
- Warm, qualified inbound leads
- Existing customer renewals and expansions
- Remote work capability
- Predictable, manageable pipeline
- Minimal rejection and cold outreach
There’s nothing wrong with this preference. These reps can be incredibly valuable for the right stage and motion. But if you’re expecting them to transform into hunter-closer-relationship-builder hybrids, you’re setting everyone up for failure.
The data backs this up. According to Emergence Capital’s survey of 600+ B2B venture-backed startups, only 27% of B2B customer meetings happen in person today. Think about that—even though companies like Toast, Brex, and Splunk are seeing 3X conversion rates from in-person meetings, 73% of interactions are still happening virtually.
Why? Because most sellers gravitate toward what’s comfortable and efficient for them, not necessarily what’s most effective for closing deals.
The Full-Stack AE Myth
The “full-stack Account Executive” has become the unicorn everyone wants to hire. These mythical beings can cold call, run complex demos, negotiate enterprise deals, and maintain strategic relationships all while hitting 120% of quota year after year.
Here’s the reality: In B2B, the full-stack AE remains a rarity.
I’ve met a handful in my career. Most people who are great at one motion are mediocre at others. The skills that make someone excellent at outbound prospecting (high activity, rejection resilience, always hunting) often conflict with the skills needed for complex deal management (patience, strategic thinking, relationship nurturing).
Rippling’s Matt Plank discovered this truth as they scaled from 4 to 30 products. Initially, they convinced themselves that if a rep couldn’t keep up with new product launches, “maybe they weren’t cut out for the job.” They thought any good rep should be able to sell all 30 SKUs equally well.
This was, in Matt’s words, “a painful learning.” Even their best reps couldn’t absorb information about new product suites effectively. The breaking point came when they launched their finance suite and started competing with companies like Brex and Ramp—suddenly they needed specialized knowledge and different buyer relationships.
Now Rippling runs three distinct sales teams: core new logo reps, account managers, and specialized product AEs who get tagged in for complex deals. Each team does what they’re wired to do, instead of forcing everyone to be everything.
As Matt puts it: “You can teach a revenue-oriented person to have empathy for a customer. You can’t make, at large, a CSM org want to be a quota-carrying, revenue-generating team.”
The Hiring Solution
So what’s the answer? If you want your sales team to do more, you have to hire exactly that.
Stop trying to mold people into roles they’re not wired for. Instead:
For Inbound Motions: Hire patient, consultative sellers who excel at qualification and deal progression. They should love long sales cycles and complex decision-making processes.
For Outbound Motions: Hire hungry, resilient prospectors who thrive on activity metrics and don’t take rejection personally. Volume and persistence matter more than relationship-building skills.
For Field Sales: Hire people who genuinely enjoy travel and face-to-face relationship building. Toast learned this the hard way—they found that promoting from within often worked better than external hiring. 25% of their sales organization got promoted in the last 12 months, and many of their best field reps came from non-traditional backgrounds: teachers, military veterans, and people from the restaurant industry itself.
Why did these unconventional backgrounds work? Because these people were already comfortable with face-to-face interactions and understood the value of building local relationships. The former teacher knew how to explain complex concepts in person. The military vet understood discipline and territory management. The restaurant industry hire already spoke the customer’s language.
Toast’s CRO also discovered something fascinating: they teach their reps to become the “mayor of their town” by building deep local relationships. But you can’t coach someone into wanting to be a local relationship builder—you have to hire for it.
Loren Padelford, CRO of $100M+ ARR Slice, put it perfectly: “The best reps just work much, much harder. And they are truly curious. That’s rare.” The top performers are constantly learning more about their customers, the product, and the industry. Most reps aren’t wired this way—they sort of worked for a while during the easy money years of 2019-2021, but that doesn’t work today.
You can’t coach curiosity. You can’t train work ethic. These are fundamental traits that either exist or they don’t.
For Strategic Accounts: Hire relationship builders who think in terms of years, not quarters. They should have experience managing complex stakeholder groups and navigating organizational politics.
Gong’s ex-SVP of Sales Jameson Yung learned this lesson while competing head-to-head with Chorus in the early days of conversation intelligence. Both products were similar, but Gong won by making a crucial hiring decision: “When I joined Gong, I immediately raised quotas and compensation and hired a sales team one or two levels above what they initially thought they’d put in place.”
Why? Because “you can’t really put junior sales reps on the phone with CROs and expect massive success.” Gong hired people “somewhere between the 20-years-in-a-suit and the year-or-two-on-the-job person”—experienced enough to handle executive conversations, but scrappy enough to grind.
The result? They outsold Chorus from the start and built a $7.5B company. Not through better technology or marketing, but through hiring exactly the right people for the motion they needed.
The Bottom Line
The fastest way to miss your number is to hire for one motion and expect another. The second fastest way is to keep trying to coach people into becoming something they’re fundamentally not.
Kyle Norton, CRO of Owner.com (and former leader of a $1B business unit at Shopify), has a concept that applies perfectly here: “minimum effective dosage.” He’s talking about RevOps, but the principle holds for sales hiring. You want just enough of the right people to drive results, but not so much complexity that you spend more time managing the mismatch than building the business.
Your sales team will do exactly what they’re wired to do, regardless of what your growth strategy demands. Plan accordingly, hire specifically, and comp appropriately.
The companies that figure this out scale efficiently. The ones that don’t burn through sales talent and wonder why their numbers keep coming up short.
