Midyear is your leverage point.
This diagnostic strategy session helps growth-stage leaders quickly identify the root issues behind scaling strain, and build an actionable plan to fix them fast.
You don’t need more noise. You need a clear read on what’s actually slowing you down. I bring a decade of operating experience inside high-growth B2B teams, translating sharp strategy into practical, people-aware execution.
This session is engineered to help you course-correct before cracks turn into chaos & derail what you've built.
Ready to fix what's not working?
Let’s get you out of the weeds and into an scalable strategy that supports your growth.
Why Now?
Midyear is your window.
Wait until Q4 and urgency takes over with goals to hit, deals to close, and no room to recalibrate.
Fixing what’s not working now protects:
- Your delivery quality and client trust
- Your team’s capacity and energy
- Your margins, planning, and momentum heading into year-end
Who It's For
This session is for founders, execs, and growth-stage leaders at B2B companies who:
- Are scaling quickly but feeling friction in ops, delivery, or team capacity
- Know there’s a deeper misalignment, but can’t quite pinpoint it
- Don’t need a 6-month engagement. Just clarity, fast.
What We’ll Do
Session 1: Strategy Diagnostic (60 minutes)
We’ll dig into the real issues behind what’s not working. Systems, roles, incentives, handoffs, decision rights: you name it. You’ll leave this session with laser focus on the actual friction points, not just surface-level symptoms.
Session 2: Action Mapping (60 minutes)
We’ll turn that clarity into a grounded, strategic action plan: what to clean up, what to kill off, and what needs to shift so your business can run more sustainably.
What You’ll Walk Away With
- Clear diagnosis of what’s slowing your business down
- Strategic priorities with resource considerations, not just a list of recommendations
- A custom Action Map aligned to your growth stage, capacity, and goals
- Confidence in what to do next & what not to waste time on
The Impact
A COO at a $15M B2B services company came in thinking they had a workflow issue. What we uncovered: their sales team was closing deals with unrealistic timelines, and ops was constantly in scramble mode. We rebuilt the prioritization filters, clarified decision rights, and mapped a realistic scope. Within a month, delivery stabilized, team capacity was back on track, and they avoided a $120K hire they didn’t actually need.
“Sadie helped us find the problem under the problem, then fix it before bleeding more time and money.”
What Clients Say
"This session gave me clarity I didn’t know I needed. We thought we had a delivery issue. Sadie helped us trace it back to a misalignment between sales incentives and ops capacity. We implemented changes she suggested in a week, and the business and team were back in lock-step."
"I finally understood what was actually slowing us down. Sadie helped us isolate the real blockers in our internal process and cut through noise. I didn't realize how distracted I'd been solving the wrong problems. We avoided a costly hire and got our margins back on track."
"Sadie saw the system faster than anyone I’ve worked with. She helped us name what wasn’t working in a way that made the next step obvious and actionable."
$1,200 Investment
About Sadie Shepard
I’m a strategic advisor and former operator with 10+ years inside growth-stage companies, helping founders, execs, and functional leaders untangle what’s not working and make decisions that actually hold.
I’ve led post-merger integrations, scaled customer success programs across eight legacy orgs, restructured sales ops at $60M+ in ARR, rebuilt brand trust in down markets, and designed team structures that protect energy and margin as companies grow.
That’s why I built this session: to give you a sharp, grounded way to fix what’s off *before* it drains your team, stalls your delivery, or derails your momentum.
Want to see more of how I work? Explore my advisory work here.