ScalingCFO

Have You Scheduled Your Annual Strategic Planning Session?

By Cruz Gamboa, CEO & Founder, ScalingCFO · · 4 min read

By Cruz Gamboa Strategic CFO | Scaling Up Coach Founder, Ascend Growth Ventures

If you are a company with revenues between $3M–$10M and fewer than 50 people, growth alone isn’t the goal. Sustainable, strategic, scalable growth is.

That’s why our clients don’t just “set goals for the year.” They run an Annual Strategic Planning Session—a 2-day reset to install the structure, people, and rhythm needed to scale with purpose.

This isn’t corporate theater.

It’s how founder-led businesses prepare to break through the next ceiling.

Here’s a behind-the-scenes look at how we run it at Ascend Growth Ventures—using the Scaling Up methodology plus deep financial clarity, mindset alignment, and AI leverage.

4 Weeks prior: Design the Business You Want

1. Set the Tone: Founder Reset

We begin with a conversation with the founder or CEO to get clarity at the top:

  • What’s your 3-year vivid vision?

  • Where are you still acting like the Operator vs. Architect?

  • What should you delegate that is not in your zone of genius?

  • What are the areas of opportunity for automation and AI?

  • What is your definition of success for next year?

  • What do you think is working well in your company?

  • What are the areas of improvement?

  • We go over your historical and forecasted results and ask questions.

  • We review your org chart and get clarity on the effectiveness of your leadership team.

Founders don’t scale businesses. They scale themselves—and the business follows.

Day 1: 2. Strategic Growth Check-in (Scorecard + KPI Review)

We get honest.

  • What moved the needle this year?

  • What did we ignore, delay, or avoid?

  • What metrics actually drove performance—and which ones were noise?

  • We review the objectives of the session and what everyone wants to get out of it.

Day 1: 3. The People Review: Right People, Right Seats

We run a full talent calibration:

  • Core Values Check – Are these alive or decorative?

  • Functional Accountability Chart (FACe) – Who owns what outcomes?

  • Performance Grid – Each team member is assessed on results, alignment, and coachability.

Then we ask the hard question:

“Would we hire them again for this role, knowing what we know now?”

If the answer is no—we plan the shift.

4. Strategy Deep Dive

This is where most founders play small. We push for clarity and boldness:

  • One-Phrase Strategy / Brand Promise

  • Key Process Flow – How do you make money? Where’s the margin?

  • BHAG + 3-Year Targets

  • SWOT + Strategic Initiatives

  • What is your flywheel for next year?

We identify the 2–3 levers that will unlock disproportionate growth this year. And we link them to profit—not just activity.

We finish with a team event to bring the group closer.

💰 Day 2: Translate Strategy Into Execution

5. Cash & Financial Storytelling

“You don’t run out of ideas. You run out of cash.”

We review:

  • Cash Conversion Cycle and 4 Forces of Cash Flow

  • Pricing, margin, and contribution per product/client

  • Power of One levers (1% change in 7 key drivers)

We turn finance into strategy—and give the founder a clear line of sight into profit per seat, revenue per head, and cash runway.

6. Execution Rhythm

Now we install a cadence of accountability:

  • Weekly tactical meetings with clear scorecard updates

  • Monthly strategic reviews tied to KPIs

  • Quarterly planning cycles to adjust focus

  • Daily huddles if needed to drive alignment

This is how the vision stays alive past January.

7. AI & Intelligent Leverage Review: Buy Back Time, Increase Throughput

Scaling today isn’t just about headcount. It’s about leveraging AI, automation, and intelligent systems to multiply impact—without multiplying effort.

In this segment, we ask:

  • What tasks are still manual, repetitive, or low leverage?

  • Where can AI or automation buy back time for the founder or team?

  • What workflows are breaking as we grow—and which systems must evolve?

  • How does automation tie to the company's strategy?

  • What current constraints or bottlenecks of the strategy would be clear if automated?

This is where smart founders stop hiring for tasks— and start designing self-managing systems that scale without them.

We walk away with a prioritized AI leverage roadmap for Q1.

8. One-Page Strategic Plan & Communication

We wrap by completing:

  • Annual Plan (Top 3–5 priorities and critical numbers)

  • Q1 Plan (Rocks/OKRs, Targets, and Owners)

  • Execution Calendar and Meeting Cadence

  • Cascading Message (How leaders will roll this out to the team)

The founder leaves with a battle-tested One-Page Strategic Plan and a plan to drive it forward.

🧠 Final Thought: Scaling Isn’t More Work. It’s Better Design.

An Annual Planning Session isn’t just about goals. It’s about who you’re becoming, how you’re building, and what’s in the way of scale.

The best part? Founders walk away feeling calm, clear, and back in control.

Isn't that what you really want in the end?

Want This for Your Company?

We run these Strategic Planning Sessions with $3M–$10M founder-led businesses. You bring your leadership team—we bring the frameworks, financial clarity, and pressure-tested agenda.

If you want to:

Originally published on LinkedIn.