Drew Chapin

CMO | B2B SaaS & AI | Scaling businesses to $1B+ and beyond

Westlake, Ohio, United States

About

With over 25 years in tech marketing and 14 years as a CMO, I specialize in scaling B2B SaaS and AI organizations from $100M to $1B+. I believe that marketing doesn’t win in a vacuum, winning requires alignment across the GTM machine and a relentless focus on how buyers actually find solutions today. My focus: Modern GTM and AI Transformation: I lead teams through the shift from tactical, random acts of marketing to modern, integrated marketing models. This includes the move into Generative Engine Optimization (GEO) and Answer Engine Optimization (AEO) to ensure companies remain visible where the next generation of buyers is searching. Scaling at Pace: I have a proven track record scaling Hyland from $230M to over $1.1B and recently rebuilding and modernizing the entire marketing function at Certinia. Organizational Health: I am a practitioner of The Table Group (Patrick Lencioni) methodology. I believe a healthy, aligned team is the ultimate competitive advantage. I focus on building cultures that are humble, hungry and smart. Strategic Positioning: Strong, differentiated positioning is the cornerstone to a winning GTM strategy. Using frameworks like those from April Dunford and Emma Stratton, I help companies find their unique edge in crowded AI markets, ensuring the positioning and messaging is clear, differentiated and tied to revenue Core Philosophies: Team 1 over Silos: The GTM engine and Product must function as a cohesive unit with a shared scoreboard. AI and offshoring as an Accelerator: I view the organizational impact of AI and offshoring as a growth accelerator first. The most successful companies will leverage AI and offshoring to increase workforce efficiency AND effectiveness while keeping the human element of brand and strategy at the center. Discipline and Leadership: My leadership approach combines operational discipline with the empathy required to lead large, global organizations through change. I enjoy connecting with CEOs, CMOs, Founders and Board members who are looking to scale their GTM operations and navigate the complexities of the AI-first marketing era.

Experience

  • Strategic Advisor at 2X
    Feb 2026 - Present · 6 mos

  • Chief Marketing Officer at Certinia
    Mar 2024 - Mar 2026 · 2 yrs 1 mo

    - Led all aspects of marketing at Certinia including demand generation, digital & web, product & solution marketing, content, campaigns, field marketing and customer marketing. - Rebuilt and modernized entire marketing function including key leadership hires, re-platform and relaunch of website, relaunch of 6sense, re-platform of MAP, offshore capacity expansion, implementation of integrated campaign model and ABX motions and AI training/enablement initiative for entire organization.

  • Chief Marketing Officer at Hyland
    Jun 2012 - Mar 2024 · 11 yrs 10 mos

    - Led all aspects of global marketing at Hyland, including demand generation, brand & creative, corporate communications, digital/web, product marketing, industry marketing and marketing operations. - Led Hyland marketing through several transformations during a period of significant growth and value creation. Hyland revenue grew from $238M to $1.1B+ during tenure.

  • SAP ()
    • Vice President, North America Field Marketing
      Jun 2010 - Jun 2012 · 2 yrs 1 mo

      - Led North America Marketing team for SAP BusinessObjects Business Analytics solutions. June 2010 to Dec 2010 - Led North America Marketing team for SAP Growth Solutions and Services. Jan 2011 - November 2011. - Head of SAP North America Marketing team for SAP Solutions: Mobile, Cloud, Analytics, Database & Technology, CRM, HCM, Supply Chain, Procurement, Manufacturing, SAP Services & SRS. November 2011 - June 2012.

    • Senior Director, North America Field Marketing
      Jul 2008 - Jun 2010 · 2 yrs

      - Led the North America Field Marketing team for Business Analytics (SAP BusinessObjects)

    • Director, Field Marketing
      Sep 2005 - Jul 2008 · 2 yrs 11 mos

      Led the North America Large Enterprise Field Marketing team

  • Senior Marketing Manager at Computer Associates
    Apr 2004 - Jun 2005 · 1 yr 3 mos