Get your free personalized podcast brief

We scan new podcasts and send you the top 5 insights daily.

When Checkr's enterprise outbound motion wasn't working, it wasn't a single issue. It took 1.5 years of tinkering with people, processes, and strategy to diagnose and fix all the underlying problems, highlighting that there are no silver bullets for complex go-to-market challenges.

Related Insights

The most common GTM mistake is hiring execution-oriented leaders who force a pre-existing playbook onto a new company. Each company's customer journey is unique and requires a first-principles approach to design a GTM motion, rather than cutting and pasting a strategy that worked elsewhere.

Most go-to-market challenges, from low conversion rates to departmental friction, can be traced to the handoff process between marketing and sales. Start your diagnosis here to find the root cause of issues like low-quality leads or poor pipeline velocity, not just the symptoms.

Successful ABM requires more than just marketing execution. The entire organization, including sales, implementation, customer success, and support, must be equipped to handle enterprise-level accounts. Without this cross-functional readiness, marketing's efforts to drive enterprise demand will be wasted downstream.

The primary reason new outbound initiatives fail is not a bad channel mix or messaging, but a lack of leadership commitment leading to "fits and starts." Companies quit before the cumulative impact of prospecting can materialize because they expect instant results. Success requires an unwavering organizational commitment to sustained, daily activity despite initial low returns.

When revenue lags, the common reaction is to hire more reps. This compounds the problem by adding cost to a broken system. The correct sequence is to first diagnose commercial maturity, then fix the underlying infrastructure like sales processes, and only then add headcount capacity.

Successfully challenging an incumbent in the enterprise market is not just a sales initiative. Checkr required a literal "handshake around the table" from engineering, product, legal, and GTM teams to ensure universal commitment and resource allocation for the strategic shift.

Don't assume large, well-resourced companies have solved fundamental GTM challenges. Even at Google, sales and marketing alignment is a persistent people and process issue, not one that can be solved simply by adding budget or headcount. These problems are universal.

Companies with long, complex enterprise sales cycles often mistakenly apply short-term lead generation tactics and metrics. This mismatch between a brand-building, long-term motion and a demand for immediate leads is like fitting a square peg in a round hole and is destined to fail.

Customer issues are rarely isolated events. They often originate from internal process or technology failures. When an employee lacks access to the right data or faces a flawed internal system, the negative impact is directly transferred to the customer. Fixing CX requires looking inward at employee tools and journeys first.

Companies stay stuck in failing models for three reasons: 1) The system rewards controllable but ineffective activity (more calls, more MQLs). 2) Leaders fear the perceived risk of foundational change. 3) A culture of urgency favors quick tactical fixes over addressing deep, systemic issues.