If you’ve ever closed a big deal only to see the customer churn within months, this episode covers why onboarding is the silent revenue killer. You’ll learn how to protect lifetime value, align sales with customer success, and avoid the costly mistake of ignoring the post-sale experience.
What Causes Onboarding Failures?
Most companies don’t lose customers because their product fails. They lose them because the transition from sales to onboarding breaks trust. Excitement built during the sales process quickly fades when:
- The onboarding team isn’t aligned with the promises made in sales
- Metrics focus only on the new pipeline, not customer retention
- Departments operate in silos, leaving the client to manage the gaps
Sarah Shepard, StringCan’s COO, shared her own payroll provider nightmare. The sales process was smooth, but onboarding was disorganized and frustrating. “I went from excited to dreading the partnership before we even started,” she explained. Such early disappointment can damage trust and long-term revenue.
Why Mid-Market Leaders Can’t Ignore This
Jay Feitlinger, StringCan’s CEO, recalled working with a multi-billion-dollar enterprise that invested heavily in marketing to replace customers who had churned. The leadership team refused to address onboarding problems because that wasn’t “their department.” The result was wasted marketing spend and massive attrition.
Mid-market firms don’t have that luxury. Every customer counts, and losing one because of onboarding gaps isn’t just lost revenue. It’s lost referrals, wasted sales effort, and brand damage that lingers.
Shifting the Metrics That Matter
If your scorecard is all about pipeline and closed deals, you’re measuring the wrong things. Instead, Sarah and Jay suggest focusing on:
- Customer lifetime value: Are clients staying and growing with you?
- Customer outcome achievement rate: Are they getting what they expected?
- Onboarding consistency: Is the handoff seamless between sales, success, and support?
As Jay put it: “If your sales team closes a client on bells and whistles you can’t deliver, you’re setting yourself up for failure. Radical candor up front protects both sides.”
How to Create Smooth Onboarding
The best companies treat onboarding as part of the revenue engine, not an afterthought. Start by:
- Aligning marketing, sales, and customer success with shared revenue goals
- Slowing down the sales cycle, if needed, to set realistic expectations
- Collecting desired customer outcomes during the sales process and carrying them into successful conversations
- Breaking down silos with RevOps or cross-functional scorecards
Sarah summed it up perfectly: “Slow is smooth, and smooth is fast. Retaining the right customers is where profit and referrals live.”
FAQs CROs Ask About Onboarding
Q: What’s the biggest risk of bad onboarding?
A: You burn trust before the relationship even begins, making churn almost inevitable.
Q: How can I measure onboarding health?
A: Track customer outcomes at 30, 60, and 90 days, not just implementation speed.
Q: Should sales be involved after the deal closes?
A: Yes. Sales should pass along customer goals, not just contract details.
Q: What’s the role of marketing in onboarding?
A: Marketing should validate whether promises made in campaigns align with customer success stories.
Q: How do referrals connect to onboarding?
A: Delighted customers tell 10+ peers. Poorly onboarded ones do the same, only with complaints.
Customer onboarding is not a back-office function. It’s revenue protection. When sales, marketing, and customer success align on customer outcomes, lifetime value and referrals increase dramatically.
For the full breakdown and actionable tips, listen to the Revenue Rewired Ep 27 on Apple, Spotify, Amazon Music, or YouTube. And if you’re ready to fix your revenue engine, connect with our team at StringCan Interactive.
