How it works

Every company’s post-sales situation is different, but the patterns are surprisingly consistent. Upside provides VP-level strategic guidance through three flexible engagement modes, shaped around what you actually need rather than a rigid programme structure.

Why existing options fall short

Getting post-sales wrong is expensive. Getting it right is transformational. The wrong hire or no hire at all costs you 12+ months and £200K+. The right foundation turns post-sales into your biggest growth lever.

Option A
Senior CS Hire
Hasn’t built from scratch. Often a manager who hasn’t been hands-on for a while
Wants seniority fast, not ongoing portfolio management. Decisions less objective
Hunger is hit and miss
£150–250K + £30–50K recruiter + large equity
12+ months and £200K+ if it’s the wrong hire
Option B
Figure it out internally
The person closest to the problem is often the least able to see it objectively
Easy to keep optimising what exists rather than redesigning for where you’re heading
Problems compound quietly before they show up in the numbers
The better path
Upside
Operating model built by someone who’s done it from $5M to $1B
Neutral expert perspective with no internal politics or empire-building
Hands-on, not just advisory. Embedded with the team
Flexible: from focused sprints to ongoing leadership
Lower risk than a senior hire
You keep the framework after I step back

Three ways to work together

1

CS Leadership

Hands-on, part-time CS leadership. I own the function on working days, make the hard calls, build or rebuild the operating model. I’m not advising from the sidelines. I’m in the detail, coaching the team, designing the motions, and driving execution.

Best for:
Building a CS function from scratch
Transforming an underperforming post-sales function
Bridging to a permanent CS hire
Typical activities:
Set strategy and make decisions day-to-day
Build or rebuild the operating model
Coach and develop the existing team
Design renewal, expansion, and risk processes
Build metrics and reporting
Hire and structure the team as needed
2

Targeted Advisory

Focused engagements around a specific problem or deliverable. Scoped to need, not a rigid multi-week programme. Typically shorter and more focused than CS Leadership. The right choice when you know what needs fixing and need an expert to design the solution.

Best for:
Renewal process redesign
Customer segmentation
Hiring your first CS leader
Investor-ready metrics
Expansion motion design
Risk management playbooks
3

Strategic Retainer

Ongoing strategic input following any other engagement. Regular review cadence, sounding board, and pressure-testing as the company scales. VP-level strategic guidance at a fraction of the cost, so the CS function doesn’t drift after the engagement ends.

Includes:
Monthly strategic CS review
CSM coaching and development
Quarterly business review
Hiring and scaling guidance

Who this is for

Upside serves B2B SaaS companies across a continuum of post-sales maturity. The core need is the same, but the starting point varies.

Building from scratch

✓B2B SaaS at £1–15M ARR
✓Founder still involved in post-sales and renewals
✓No dedicated CS leader or function yet
✓Churn or missed expansion hurting growth
✓Approaching or recently completed a funding round

Scaling what exists

✓Established CS team and CS leader already in place
✓Post-sales function has plateaued or isn’t delivering
✓NRR underperforming benchmarks for your stage
✓Expansion flat despite a growing customer base
✓Ownership unclear across CS, support, and sales

If any of this sounds familiar, a conversation is the best place to start.

No pitch, just a conversation.

tom@upsidecs.co.uk | +44 7970 346877