Summer’s officially in the rearview mirror. And if you’re like most B2B founders and executives, you probably spent the last few months telling yourself you’d “get to it.” Or just heads-down on dealing with issues.
Well, Labor Day just passed. So let’s talk about what you’ve been avoiding.
The Four Hard Truths Every B2B Leader Needs to Face — This Week
1. That VP Who Never Hit Plan? It’s Time.
You know the one. They’ve missed their number three quarters running. You keep telling yourself they’ll turn it around, that they just need “one more quarter.” But deep down, you know the truth: if they haven’t figured it out by now, they’re not going to.
Here’s what I’ve learned after 20+ years in B2B: Great VPs hit their numbers. Good VPs miss occasionally but recover fast. Everyone else? They’re just expensive hope.
The longer you wait, the more damage you do to your team’s morale and your company’s momentum. Your top performers are watching. They’re wondering why standards don’t seem to matter. Make the call this week.
2. Your Release Velocity Is Still Broken
Remember that big initiative to ship faster? The one you announced in Q2? If you’re honest, releases aren’t going out meaningfully faster than they were six months ago.
This isn’t just a product problem—it’s a competitive moat problem. In today’s market, velocity wins. While you’re debating feature specs in endless meetings, your competitors are shipping, learning, and iterating.
The fix isn’t more process. It’s less. Cut your release cycle in half. Ship smaller increments. Get comfortable with imperfection. Your customers would rather have 80% of what they need today than 100% of what they need next quarter.
3. AI Isn’t Going Away (And Your Competition Knows It)
Six months ago, you could get away with saying “we’re exploring AI capabilities.” Today? That’s not enough.
Your competitors aren’t just talking about AI—they’re shipping it. And if you’re not careful, they’re going to own the narrative in your category while you’re still forming committees and writing strategy docs.
Stop planning and start building. Pick one use case. Build an MVP. Ship it to a small cohort of customers. Learn fast. Iterate faster.
4. That “Critical” Hire You Keep Talking About
You know the role. The one that’s been “top priority” for the last four months. The one you discuss in every exec meeting but somehow never quite get around to closing.
Maybe it’s a head of sales, a VP of engineering, or a CMO. Whatever it is, your procrastination is costing you more than the salary you’re trying to save.
Great talent doesn’t wait around. The longer you take, the more you signal that the role (and your company) isn’t actually that important. Make the offer. Close the candidate. Move forward.
The September Sprint
Here’s your homework for this week—not next month, not next quarter, this week:
- Tuesday: Have the conversation with that underperforming VP. Don’t wait for their next 1:1. Schedule it today.
- Wednesday: Cut one step from your release process. Not eventually—literally remove it from your next sprint.
- Thursday: Pick your first AI feature and assign someone to build an MVP by month-end.
- Friday: Make the offer to your top hire candidate. Stop negotiating with yourself.
Why This Matters Now
We’re heading into Q4—the quarter that will define your year and set the tone for 2026. The decisions you make (or don’t make) in September will echo through the next six months.
Your competitors aren’t taking a break. Your customers aren’t getting less demanding. The market isn’t slowing down for anyone.
Summer’s over. It’s time to act like it.
The companies that win in SaaS aren’t the ones with perfect strategies—they’re the ones that execute relentlessly on good strategies. Stop planning. Stop optimizing. Stop waiting for perfect conditions.
Make the hard calls. This week.
Your future self will thank you. Your team will respect you for it. And your numbers will reflect it.
Now stop talking, reading and … well … stalling. Go make something happen.
