REVENUE IS BUILT BEFORE IT IS BOOKED.
Snakes & Ladders maps culture to revenue.
Every tech company has a formal revenue system: strategy, process, methodology, data and technology. But that system can only perform as well as the culture it runs on.
Culture determines which information reaches leadership, which behaviours are rewarded, how customers are treated and whether problems are surfaced while they are still solvable or given their own slide in the next quarterly business review. AI will compound the culture - for good and for ill.
Eventually, all of that reaches the number.
Revenue is what your culture becomes.
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WHAT, PRAY TELL, IS THIS ALL ABOUT?
Snakes & Ladders examines the commercial outcomes of organisational behaviour.
Tech, and particularly tech sales, is bonkers. It is equal parts brilliant, deranged, rewarding and exasperating. The intersection of incredibly cool technology and eye-watering amounts of shareholder money remains a privilege to be part of.
It also creates some fascinating operating conditions.
When incentives, power and information flow work well, revenue orgs make better decisions, serve customers properly and build commercial capacity that compounds. When they do not, the same systems produce unreliable forecasts, regretted attrition, expensive customer experiences and a surprising quantity of internal theatrics.
These are usually dismissed as “people issues” until someone notices it start consistently showing up in the pipeline.
Snakes & Ladders traces that journey. It explores:
how leadership choices and incentives shape commercial behaviour;
why sales symptoms often reveal wider organisational problems;
how internal culture reaches customers;
where power, accountability and apparently objective processes go wonky;
how healthy cultures create better information, judgement and execution;
why AI will amplify an organisation’s existing culture rather than politely replace it.
This is not a collection of workplace horror stories with the company names removed. It is an examination of the systems underneath them, why the same patterns repeat and what commercially serious leaders can do differently.
If you’re an IC you should recognise the behaviour. If you’re a CRO, you should recognise the revenue system operating beneath it.
A FEW OPERATING ASSUMPTIONS
Culture is not fluffy corporate decoration. It influences how the revenue org makes decisions and executes.
Dignity is not a perk.
Sales culture debt is real, and it compounds.
Healthy culture creates commercial capital, and that compounds too.
Company values only matter when they survive contact with incentives.
Decisive, effective revenue leadership and not being a dick are mutually inclusive.
WHO’S BEHIND THIS?
I’m Helen Mason, a British senior sales leader who has worked in tech since 2005 and led sales teams for more than 15 years.
I have led Enterprise, Commercial, Digital Native and SDR teams across UK and US-headquartered companies. My supporting evidence includes six President’s Clubs, three IPOs, one kind-of completed(ish…) degree in Social Psychology from the Open University and a current Chief Revenue Officer programme at Cambridge Judge Business School, University of Cambridge.
This combination has left me professionally incapable of watching a company treat culture as something separate from revenue performance without asking an awkward follow up question.
I am also an openly gay woman with an enduring interest in equity of opportunity, organisational power and the curious ability of apparently neutral systems to develop highly specific preferences.
I do all of this while looking unnervingly like Shiv Roy from Succession.
DISCLAIMER
Situations discussed in Snakes & Ladders come from a variety of sources, and, on the odd occasion, from my own experiences. Experiences I’ve been aware of IRL have had key parts of the story changed to protect the innocent, the guilty, and me (I don’t want to get sued). Anything that could identify people and companies has gone through rigorous changes and reframing to keep the substance of the situation accurate, but remove any chance of people and companies being identified. Any similarity to an actual real-life situation is both coincidental and expected - the examples and stories I discuss are ones that many people will recognise since they are common byproducts of misaligned incentives and wonky systems.
