The First 100 Days: How to Succeed After a Business Acquisition

What does life really look like after you buy a business? The first 100 days can be full of highs, lows, pitfalls, and lessons. In a recent conversation with Kale from Scaling Ventures, we explored the journey of stepping into the CEO role and navigating those critical early months.

Setting the Stage

Kale’s background is rooted in B2B SaaS. From sales leadership roles in New York City to consulting, operating, and private equity, his journey led him into independent acquisitions. Scaling Ventures was born from a belief in inverting the traditional buyout model: rather than giving advice from the sidelines, Kale’s team steps in as transformation agents.

They focus on niche vertical SaaS firms — founder-led, bootstrapped businesses with loyal customers but limited go-to-market execution. After acquiring and exiting a CRM for wedding photographers, Kale and his team recently completed another acquisition in the furniture and lighting manufacturing category. Just 100 days in, the lessons were fresh.

Choosing the Right Business

Kale emphasized prescriptive, data-driven filters.

• Logo retention is the number one metric. If customers don’t leave, the product has clear utility.

• Avoid explosive growth categories vulnerable to venture-backed entrants.

• Focus on stable, mature industries behind the digital adoption curve.

• Ensure profitability, the business must afford to buy itself.

• Look for founder-led businesses where empathy and product strength are strong, but go-to-market is underdeveloped.

The sweet spot is businesses with enduring utility, low customer churn, and room for structured growth.

Hardest Part of the First 90 Days

Onboarding yourself while onboarding a team creates a unique challenge.

• Many assumptions from diligence prove flawed due to poor systems of record.

• Data cleanup becomes the first priority: tidy the tech stack, fix bookkeeping, CRM, and support records.

• Operate on clean data for 60 days before resetting the plan.

• Adopt a beginner’s mindset: unwinding confidence built in diligence is key.

As Kale put it, “your number one objective in the first 90 days is don’t break the business.”

Stability, Learning, and Transition

The mantras of Scaling Ventures reinforce this:

• Focus creates the space for performance

• Simplicity is mastery

• Shower off your ego

Overhauling too much at once risks breaking the business. Instead, stability and observation dominate the first 100 days. Document processes, extract tribal knowledge, and introduce repeatable systems.

Building Trust with Customers and Team

Trust tests appear quickly:

• Customers may push on payment terms.

• Vendors may tighten conditions.

• Teams may worry about layoffs.

Kale’s answer: transparency. Tell the truth, share plans, communicate outcomes, and invite conversations. Visit customers, survey them, and gather feedback.

With teams, avoid premature head-count cuts. Establish clear performance standards, connect roles to goals, and align everyone to the one most important priority. The result should be a team “jumping out of their seats fired up” and customers reassured.

Watch the Full Webinar with Kjael Skaalerud

For the complete conversation, insights, and all the nuggets shared, watch the full webinar with Kjael Skaalerud of Scaling Ventures on our YouTube channel. It covers everything discussed here and more from the first 100 days, trust tests, data cleanup, and strategy development to pricing, onboarding, and team structuring.

Structuring a Lean, High-Performance Crew

Scaling Ventures prioritizes lean, tech-enabled teams. Three “Iron Man suits” outperform 100 in riot gear. Performance management is objective, data-driven, and aligned with company vision.

Everyone must understand the 10-year vision, three-year goals, and this quarter’s priorities. Roles are clarified, talent is directed toward areas that excite them, and feedback loops drive improvement.

Strategy Development in the First 30–90 Days

The roadmap follows three phases:

1. Day 1–30:

   • Customer communication and relationship transition

   • Sales team and personnel analysis

   • Market and customer interviews

2. Day 31–60:

   • Systems cleanup and centralization

   • Mapping the business processes

   • Establishing base rates and benchmarks

3. Day 61–90:

   • Identify constraints using the theory of constraints

   • Prioritize high-impact levers

   • Develop a simple, focused plan for growth

Growth Levers: Pricing, Onboarding, and Subtraction

Growth in the first 100 days comes less from addition and more from subtraction.

• Mastery is subtraction: remove the 80% of activities that produce little.

• Onboarding redesign: revisit first-principles, shorten timelines, assign accountability.

• Pricing and packaging: test carefully, start with new customers, then transition existing ones.

Simple changes in invoicing or payment methods can transform cash flow. Churning the wrong customers can improve overall business health.

Friends, Family, and Capital

The discussion also touched on cap tables. Kale’s belief: in buyouts with enduring, profitable businesses, inviting friends to invest can provide access to strong returns and heighten personal accountability. However, qualifying them, setting expectations, and recognizing the responsibility are essential.

Final Takeaways

The first 100 days are not about heroics. They are about:

• Stability over disruption

• Humility over ego

• Learning before acting

• Building trust with customers and team

• Cleaning systems and data before strategy

• Subtraction before addition

As Kale noted, “action removes doubt more than anything. Stay moving.”

Resources

• Scaling Ventures Sub stack— lessons and playbooks on acquisition and operations

• Recommended Reading: Buy Then Build, The Messy Middle, How to Buy a Small Business

For entrepreneurs stepping into ownership, the first 100 days are the foundation of everything to come. Focus on stability, data, trust, and simplicity and the growth will follow.

Contact us today to learn how we can support your next deal.