Field notes on the commercial work that gets a business to its next stage.

The first ninety days of an interim CCO.

The brief on day one is almost never the work that ends up moving the number. The good news is that the gap between the two is usually obvious by the end of week two — if you've gone looking for it.

Most interim mandates start with a brief that sounds like an action plan. "We need to grow pipeline." "Retention is too low." "We need to professionalise the sales team." The CEO has a hypothesis. The board has a hypothesis. The investor has a hypothesis. They are usually all different — and all partially right.

The job in the first ninety days isn't to validate the brief. It's to find the actual constraint, in the actual data, alongside the actual people, before committing to a plan. Done well, the first quarter of an interim engagement looks roughly like this.

Days 1–14: diagnose without prescribing.

Two weeks of structured listening. Pipeline meetings. CS reviews. One-to-ones with every direct report and every senior cross-functional partner. Customer calls — both happy customers and recently churned ones. Deal post-mortems. The CRM, the data warehouse, the board pack and the investor pack, side by side.

The deliverable at day 14 is a written diagnostic — six to eight pages, one chart per page, board-grade language, prioritised. The point isn't a beautiful document. The point is forcing yourself to commit, in writing, to what you believe the constraint actually is.

Days 15–45: align, then move.

Two conversations decide the next 45 days. The first is with the CEO, on the diagnostic. Where do we agree? Where do we disagree? What's politically deliverable, what isn't? The second is with the team. Diagnostics that aren't shared with the team they describe are just judgments. Diagnostics that are shared become starting blocks.

By day 30, the operating cadence should be different. Forecasting more honest. Pipeline reviews tighter. Deal hygiene stricter. Customer success measured on retention, not activity. Hires identified — even if not yet recruited. None of this is glamorous. All of it compounds.

Days 45–90: install, don't advise.

The interim trap is to write good plans and let the organisation execute them. The interim job, properly done, is to install the operating model — actually run the forecast call, actually do the deal review, actually hire the Head of Sales, actually make the unpopular call on the under-performer — long enough that it sticks after you've gone.

By day 90, the question to ask isn't "what have I done?" It's "what would happen here tomorrow if I disappeared today?" If the answer is reassuring, the engagement is on track. If it isn't, the next ninety days have just been scoped for you.

Six things to fix before a Series A diligence.

Series A investors aren't testing your product anymore. They're testing whether the commercial function around the product can be scaled. Here are the six places they look first.

By the time a business is ready to raise a Series A, the product question is largely settled. Customers exist, revenue exists, the deck looks credible. What investors actually diligence — and where rounds slow down or fall over — is the commercial function around the product. These are the six things that consistently come up.

1. Revenue quality, not revenue size. ARR is interesting. NRR, GRR and cohort retention are diligence-grade. If you can't show the curve of how a £100k cohort from 18 months ago looks today — by logo and by revenue — you're not Series A ready.
2. Customer concentration. Investors don't fear small customers; they fear top-five concentration. Map your top five and top ten customer revenue, ARR and gross margin contribution. Have an honest answer to "what happens if you lose the largest one?"
3. Pipeline coverage that's actually defensible. A 4× pipeline made of deals that have sat in the same stage for six months isn't pipeline. It's hope. Stage definitions, age-of-stage discipline and conversion-rate honesty matter more than the headline ratio.
4. CAC payback the team actually believes. CAC payback under 18 months is the ask. The number an investor cares about more is whether the team agrees on how it's calculated. Sales-loaded CAC, fully-loaded CAC and gross-margin-adjusted payback tell three different stories.
5. The shape of the leadership bench. "Founder-led commercial" is fine at seed. At Series A it's a discount. The investor wants to see a credible commercial operator who isn't the CEO — even if that's a recently hired Head of Sales rather than a CCO.
6. The commercial story, told plainly. Most decks describe what the business does. Almost none describe how the commercial engine compounds. A simple one-page narrative — segment, motion, retention, expansion, leadership — beats a forty-slide deck.

None of this is new. None of it is hard, in isolation. What's hard is doing it before the round starts, when the team is still building the product. The businesses that close Series A rounds quickly are almost always the ones that did the diligence on themselves three to six months before the investor did.

Why churn is the most investor-grade metric you have.

Retention isn't a customer success problem. It's the cleanest signal of commercial health a business can put in front of a board, an investor or an acquirer.

SaaS businesses talk about retention as if it's a customer success metric. It isn't. It's a cross-functional signal of the entire commercial system: who you sold to, what you promised, how quickly you delivered, whether the product actually worked, whether the account was set up to expand. Churn is the clean output. Everything that touches the customer is the input.

That's exactly why investors love it. Pipeline can be inflated. New ARR can be discounted into existence. CAC can be argued about. Retention can't easily be faked. Either last year's £100k of ARR is still £100k this year, or it isn't. Either the cohort that started 18 months ago is bigger or smaller today. The shape of that curve tells an investor more about commercial credibility than any forward-looking metric in the deck.

Three retention signals that move valuation.

1. Gross retention curve by cohort. Pick a cohort — say, all customers acquired in the same quarter 18 months ago. Track their revenue today. The shape of that curve is the cleanest signal you have. Flat is good. Climbing is great. Falling is a story you'd better have an answer for.
2. Net Revenue Retention above 110%. Below 100% is a leaking bucket. 100–110% is fine. Above 110% means existing customers are paying you more this year than last year, in aggregate, and an investor can model the business as compounding before any new sales.
3. Time-to-value on new logos. A subtle one. The fastest leading indicator of next year's churn is how long it takes a new customer to start using the product the way they bought it. Faster = retained. Slower = at risk.

The reason retention is so investor-grade isn't ideology. It's that retention quietly audits everything else. The companies I've worked with that lifted retention from 68% to 95% — over 18 months, under leadership team accountability — didn't just save customers. They reset what the business was actually capable of selling, and to whom. The valuation uplift on exit took care of itself.

From founder-led to founder-free: graduating the commercial function.

The hardest hire a scaling founder makes isn't the next engineer. It's the first commercial leader who isn't them. Most do it too late. A few do it too early. Almost no-one does it well the first time.

Founder-led selling is a feature in the early years. It's the founder's network, the founder's conviction and the founder's customer feel that wins the first 30, 50, even 100 customers. The trouble is that what wins those customers is exactly the thing that prevents the next 200. The motion that scales is not the motion that started the business.

The business knows this before the founder does. Sales cycles get longer. Deals stall in the founder's calendar. Customer success leans on the founder for difficult conversations. Forecast accuracy slips. The team is fine — busy, even — but the engine is no longer compounding. By the time it shows up in pipeline, the gap has been there for two quarters.

Three failure patterns when founders hire their first commercial leader.

1. Hiring for pedigree, not for stage. The CCO from a £100m ARR business often can't operate inside a £5m business. The job needs someone who has built the next stage, not run the one after.
2. Hiring without giving up the seat. A founder who hires a commercial leader and then keeps closing deals personally has hired an expensive head of sales. The transition only works if the founder genuinely vacates the chair.
3. Skipping the diagnostic. Most first commercial leaders inherit a brief — "scale the team, hit the number" — without inheriting a diagnosis. The first 30 days disappear into firefighting. The next 60 disappear into recovering from the first 30.

The cleanest way through is to bring in an experienced interim commercial leader for three to six months ahead of the permanent hire. The interim runs the diagnostic, fixes the obvious things, defines what the permanent role actually needs to be, and writes the job spec from inside the business rather than from the outside. The cost looks expensive on paper. The cost of getting the first permanent hire wrong, six months in, is materially higher.

The pattern is consistent enough across founder-led businesses that it has stopped being a coincidence. By the time the first commercial leader is right, the business is effectively a different one.