5 Critical Go-to-Market Lessons from Crosschq’s Enterprise Journey

The traditional B2B SaaS marketing playbook is dead. At least, that’s what Mike Fitzsimmons, founder of hiring intelligence platform Crosschq, shared in a recent episode of Category Visionaries. His journey offers valuable insights for founders navigating today’s evolving enterprise landscape. Here are five key lessons from Crosschq’s go-to-market evolution:

1. The Death of Traditional B2B Marketing

The standard 2016-2018 B2B SaaS demand generation strategies no longer work. As Mike plainly states, “I will tell you that I don’t even know what year to put this in brackets, but called the 2016 17-18 B2B SaaS demand gen playbook that everybody kind of runs, you know, scrap it. I just like completely throw it out.”

Digital marketing costs have skyrocketed, making traditional channels increasingly ineffective. “CAC is going through the roof and getting to a healthy sales and marketing efficiency metrics is getting more challenging,” Mike notes. The solution? A return to high-touch, personal engagement strategies.

2. The Power of Intimate Events

Instead of chasing digital leads, Crosschq has found success through small, curated gatherings. “We’re doing road shows now, literally, as we have new product releases going market to market, live roadshows with select small, intimate buying groups,” Mike explains. These events typically include around twelve carefully selected attendees, mixing existing customers, prospects, industry analysts, and ecosystem partners.

This approach extends to trade show strategy as well. Rather than investing in expensive booth space, Mike advises to “Don’t need to go wide, don’t need to have our name on the lanyard, but make sure that we’re connecting in a human way with people.”

3. The Partnership Myth

Many B2B companies fall into the trap of thinking partnerships are as simple as signing agreements and setting up referral programs. Mike challenges this assumption: “The term is so loosely used and especially in our world where you see company integrates, Company A, integrates with Company B and stand up some sort of referral agreement and all of a sudden assume they’re partners and that they’re going to be actively selling each other’s wares. It doesn’t work like that.”

Success in partnerships requires direct engagement with sales teams: “The art there is you actually have to get hand to hand combat with the actual sellers at your partner to make sure that they are incentivized to go sell your stuff.”

4. Strategic Analyst Relations

For enterprise companies, analyst relations are crucial but require a measured approach. Instead of immediately pursuing top-tier firms, Mike advises founders to “calibrate your expectations but don’t sort of stare a gift horse in the mouth and put the effort in, especially on those influencers that maybe don’t have a national brand because they truly can help.”

5. The Evolution of Sales Motions

Enterprise sales requires constant adaptation. Mike shares how Crosschq’s approach has evolved: “Sales cycles are longer, right. Sales cycles are six months now instead of one month. As you’re moving up market and moving those larger opportunities, we have absolutely seen that digital marketing wholly has become incredibly challenging.”

This shift demands a more strategic, high-touch approach. As Mike explains, “We’re certainly putting more efforts into hand to hand combat, more efforts into live events that things of that nature.” The key is moving away from the COVID-era comfort of relying solely on inbound leads and Zoom demos.

These lessons underscore a broader trend in B2B enterprise sales: the return to human connection in an increasingly digital world. While technology remains important, success in today’s market requires a more nuanced, personal approach that prioritizes genuine relationships over scalable but impersonal digital tactics.

For founders navigating the enterprise landscape, the message is clear: don’t be afraid to abandon playbooks that no longer work, focus on creating meaningful connections, and always be ready to adapt your go-to-market strategy as the market evolves.