Podcast Summary: B2B Agility with Greg Kihlström™

Episode #72: Concept to Acquisition with Chris Tilkov, DocuSketch
Date: December 2, 2025
Host: Greg Kihlström
Guest: Chris Tilkov (General Manager at DocuSketch; Creator of Ask Amy)

Main Theme

This episode explores the journey from entrepreneurial concept to successful acquisition, featuring Chris Tilkov’s transition from a hands-on technician in the restoration and insurance industry to a technology entrepreneur, with insights for B2B marketers and business leaders. The discussion covers the creation and growth of the Ask Amy platform, the challenges of scaling niche technology products, the importance of reputation and relationships, lessons learned in the acquisition process, and ongoing agility in the workplace.

Key Discussion Points & Insights

1. Chris Tilkov’s Unique Career Path (02:47–04:20)

• From Carpet Cleaner to Tech Leader: Chris began as a flood technician and carpet cleaner at 17, gradually moving into roles involving architecture, engineering, business, and technology.
• Industry Continuity: "I don't think you'll find too many millennials out there that stayed in the same industry so long." (Chris, 02:47)
• Natural Evolution: Created innovative products for former employers, including sales reporting and national estimating platforms for franchise groups.

2. Identifying the Market Need for Ask Amy (04:43–06:13)

• First-Hand Experience: Chris noticed inefficiencies in reviewing insurance estimates—both time-consuming and lacking sufficient expertise.
• Motivation to Bootstrap: Opted to start Ask Amy himself after an employer passed on the idea, leveraging his unique timing in life to take a risk.
• Market Gap: "There were not enough people, there were not enough experts. And it was a terribly inefficient process. So that was the need." (Chris, 05:16)
• Leap of Faith: Needed to build robust rules into the product before releasing it, as partial solutions were insufficient.

3. Data-Driven Product Development (06:44–07:58)

• Transition to Empirical Validation: Early traction relied on Chris’s reputation, but growth enabled clear demonstrations of time savings and improved accuracy for clients.
• Industry Impact: The platforms together now review "billions of dollars in estimates value" and optimize reimbursements for both contractors and insurers.

4. Scaling and Gaining Traction (08:35–09:46)

• Product First, Sales Second: "I am more on the technical side. So I spent a lot of time on product. It had to be right." (Chris, 08:36)
• Reputation as the Initial Brand: Relied heavily on relationships built as a trainer, speaker, and consultant in the field.
• Internal Scaling through Acquisition: Integration with DocuSketch multiplied usage, as Docusketch became the biggest user of Amy.

5. Branding, Storytelling, and Relationship-driven Growth (09:46–12:10)

• Personal Branding: "When we say we're trying to figure out if they're looking at any other products, they'll hear my name as often as they'll hear the product." (Chris, 11:34)
• Industry Relationships: Connections—such as long-standing trust with Nelson Higgins—were key to acquisition and partnership opportunities.
• Storytelling through Reputation: Early sales were fueled by industry reputation, not traditional marketing.

6. The Mindset Shift Toward Acquisition (12:10–15:05)

• Desire for Strategic Acquisition: Chris always hoped for a "non-biased, industry-wide tool" rather than selling just to one company's interests.
• Right Time, Right Fit: Docusketch’s mission aligned perfectly, and both platforms together created an unbiased, accurate system for claims estimation and review.
• Personal Timing: Acquisition close coincided with the birth of his first child. "When Docusketch ran two weeks late and my child came two weeks early, it created some intense time. So quite the week there in the end." (Chris, 14:47)

7. Lessons from the Acquisition Process (15:05–16:42)

• Well-Managed Books & Simple Pricing: Clean financials and straightforward licensing model were attractive to investors.
• Importance of Recurring Revenue: "In hindsight, to say that reliable recurring revenue is attractive to investors should be pretty obvious..." (Chris, 15:39)
• Trust and Partnership: Knowing and trusting the other founder involved made negotiations faster and smoother.

8. Advice for Marketers Across Industries (16:42–18:41)

• Learning from Larger Organizations: Chris continues to learn from the structure and scale at DocuSketch, having come from a hands-on, boots-on-the-ground background.
• Importance of Combined Expertise: Value in integrating industry, technical, and client perspectives.
• Continuous Learning: Admits he’s still absorbing broader lessons, suggesting humility and curiosity are important.

9. Staying Agile—Continuous Experimentation (18:52–19:57)

• Agility Mantra: "Some of the biggest successes in my career have been not through asking but by just doing... Always keep moving." (Chris, 19:12)
• Encouraging Creativity: Advocates for fostering environments where team members can prototype, experiment, and enact change without bureaucratic drag.
• Advice for Managers: Foster creativity and agility in teams.

Notable Quotes & Memorable Moments

• Chris on Industry Loyalty:
  "Somehow I started in this industry, restoration and insurance, when I was 17... I don't think you'll find too many millennials out there that stayed in the same industry so long." (02:47)

• Identifying the Need:
  "There were not enough people, there were not enough experts. And it was a terribly inefficient process. So that was the need." (05:16)

• On Product Integrity:
  "It had to be right. And for sales, I really ended up leaning on my reputation in the very beginning. So the product was first kind of built on the shoulders of my reputation." (08:36)

• Brand and Reputation Connection:
  "When we say we're trying to figure out if they're looking at any other products, they'll hear my name as often as they'll hear the product." (11:34)

• Acquisition Timing:
  "When Docusketch ran two weeks late and my child came two weeks early, it created some intense time. So quite the week there in the end." (14:47)

• On Agility and Experimentation:
  "Some of the biggest successes in my career have been not through asking but by just doing... Always keep moving." (19:12)

Useful Timestamps

• 02:47: Chris describes his background and early industry experiences
• 04:43: Identifying opportunity and inspiration for Ask Amy
• 06:44: Transition from anecdotal to data-driven business validation
• 08:35: Challenges of scaling, early growth strategies
• 09:46: Storytelling, branding, and industry relationships
• 12:44: Mindset shift toward acquisition and partnership fit
• 15:15: Acquisition process lessons—financials, pricing, recurring revenue
• 18:52: Staying agile: experimentation and breaking bureaucratic barriers

Tone & Language

Chris’s tone is candid, approachable, and rooted in deep industry experience. His narrative balances technical insight with humility, emphasizing practical experimentation and the human side of scaling and selling a business.

Conclusion

This episode offers a personal, strategy-rich look at product development, growth, and acquisition in B2B technology. Chris Tilkov’s journey demonstrates how deep domain expertise, personal reputation, and a willingness to experiment can power innovation, while partnerships and acquisitions thrive on aligned values and trust. Marketers and business leaders across industries will find practical lessons in agility, relationship-building, and the importance of choosing the right moment—and partners—for growth and exit.