From Bare Strategy

Writing

One idea at a time. New every week.

Strategy · April 2, 2026 · 9 min read

How to win a competitive deal when you're not the market leader

Every competitive deal is scored on a list nobody wrote for this buyer. It gets inherited from the last evaluation, or set by the incumbent on an early call, and it favors the market leader by design. Call it the inherited scorecard. Scoring higher on it is the losing game. The way through is to add a line where the buyer's real problem lives and our answer is genuinely better, then plant questions we can answer, choosing references that match the situation, sequencing the demo around what's hard to show, and naming the switching cost before they do.

Competitive Strategy Sales SaaS Competitive Deals Sales Playbook Win Rate

Strategy · April 1, 2026 · 8 min read

When to rebrand your SaaS (and when repositioning is enough)

Most SaaS companies at a growth plateau decide the brand is broken. Usually the positioning stopped matching the market, and nobody noticed because positioning doesn't look like anything. A rebrand changes the identity. Repositioning changes what you stand for and who you serve. Run the five-question diagnostic before spending six figures on the version of the work that has a deliverable everyone can see.

positioning saas branding

GTM Strategy · March 29, 2026 · 8 min read

Your free trial is not a product-led growth strategy

Most PLG attempts fail because we ship the front door and never build anything behind it. A free trial is a distribution tactic. Product-led growth is a decision about who does the selling. The thing to test before you launch a trial is the unescorted hour, and trial length has almost nothing to do with it.

plg product-led-growth free-trial saas-gtm conversion churn positioning

SaaS Growth · March 28, 2026 · 8 min read

Why your SaaS customers are churning (and it is not the product)

Four things end a subscription. The customer was never a fit and our messaging said otherwise, the customer was a fit and never got far enough to find out, the customer got value and couldn't prove it to anyone with a budget, or the product genuinely can't do the thing. Only the last one is a product problem, and it's the rarest. We rewrite the other three into roadmap items because a roadmap item is something we know how to build. Diagnose the type first, then fix in order, starting upstream.

saas churn retention positioning onboarding

Positioning · March 26, 2026 · 9 min read

How to differentiate your SaaS when every competitor sounds the same

When features converge, difference has to be claimed rather than demonstrated. There are three places to claim it. Own the customer the leader walked away from, rewrite what buyers evaluate on, or name one outcome nobody else will say out loud. Running all three at once is the thin coat, and a thin coat covers nothing.

differentiation positioning competitive saas messaging

Strategy · March 25, 2026 · 7 min read

How to build a GTM story that investors actually believe

Investors pass on GTM stories that list what a team has been doing. They're scanning for one thing, evidence that the motion repeats. The clearest proof is the same-spot test. If we can name what our motion reliably gets wrong, we have a system. If everything went well and nothing went the same way twice, we have anecdotes. Five layers carry the story, and there are honest stand-ins for every one of them at pre-seed.

gtm fundraising positioning saas investors

The newsletter

One idea in your inbox, every week.

No sequences, no funnels.