The One Thing That Everyone May Be Too Busy to Worry About: Winning

I know this sounds crazy, but quick: tell me who’s responsible in your organization for making sure the company is winning in the market.

• VP of sales? They’re losing sleep over the new bookings plan.
• VP of marketing? They’re obsessing over pipeline.
• Head of customer success? They’re fretting about GRR, NRR, or both, depending on how you’ve defined the job.
• Head of product? They’re worried about whether they got the requirements right and whether engineering is going to ship on time.
• CFO? They’re worried about the operating plan, cash, and all the ways reality might depart from the spreadsheet.
• The investors on the board? They’re worried about how you’re tracking to the model they presented to their investment committee.

Everybody has something important to worry about. And everybody can get so focused on their own thing that nobody is watching the one thing that ultimately matters most:

Are we winning the market?

And it goes deeper. Because once you're achieving all those plan targets, the conversation immediately changes to efficiency:

• VP of sales: productivity and attainment, win rates, and sales cycle length.
• VP of marketing: pipe/spend, cost/oppty, and marketing attribution.
• Head of customer success: ARR/CSM, time-to-value, and COGS.
• Head of product: R&D spend, engineering velocity, roadmap predictability, and whether anyone is actually using what you ship.
• CFO: burn multiple, free cash flow, operating margins, and every major expense line as a percentage of revenue.
• The investors on the board: Rule of 40, burn multiple, ARR/FTE, and whether the whole machine is getting more efficient as it scales.

So now we have two layers of management attention: first, did we make the plan? Then, did we make it efficiently? That's usually enough to keep any executive leadership team (ELT) fully occupied and then some.

Both layers are important. But neither addresses our simple question:

Are we winning the market?