Restoring Retention Through a Three-Company Merger
Situation
I joined to work with a former CEO partner shortly after a PE firm acquired the company. Over the following months, the firm completed additional acquisitions to merge into the business, expanding the product footprint, building AI capability, and positioning the combined company for a sale in a few years.
Challenge
Integrating three businesses at once meant reconciling different account-management practices, product roadmaps, and customer bases under real time pressure, while the core platform needed stability work to reduce churn. NDR became the company's defining metric, the clearest signal of whether the merger was working.
Approach
- Renewal, expansion, and upsell ownership moved from Sales into a newly built Customer Success function, built for sustained accountability instead of one-off wins.
- Built and trained a new CSM install-base sales function from scratch, with playbooks covering renewals, expansion, and upsell, transitioning all accounts within one quarter.
- Promoted from within to lead it rather than hiring externally (see "Liberate the Talent" on About).
- Deployed AI workflows (ChatGPT, Claude, LinkedIn Sales Navigator) across a team of 4 to analyze customer health signals, product engagement, and ticket trends at scale, giving the team the ability to intervene proactively across 300+ accounts.
- Pushed renewal rate increases averaging 5.2% against a 2% target.
Results
- NDR: 70% → 100% | GDR: 60% → 96% | Churn: 30% → 10%
- Achieved Rule of 20 in 2025, up from a $4M shortfall and 30% churn in 2023.
- Time-to-value: reduced from 6 months to 2.5 months, with some implementations reaching as low as 5 weeks.
Lessons Learned
Integrating three businesses on an aggressive timeline taught me how much sequencing matters. In hindsight, I'd push earlier and harder for a pace the business could actually sustain, instead of absorbing pressure to move faster than the fundamentals allowed.