Tracy Sestili
Chief Marketing Officer · Enterprise SaaS · AI & Category Creation
Summary
Multi-time CMO. Two exits. RevOps DNA. I've spent the last several years marketing AI products to enterprise buyers by translating technical depth into category-shaping narratives. My core strengths are building integrated GTM engines that connect brand to bookings: demand gen, ABM, product marketing, developer and technical audience strategy, MarketingOps, SalesOps, and partnerships, all wired into one revenue function. Where I've proven it: Intellimize → Webflow (2024). As CMO and CRO, I led marketing and acquisition strategy. During my tenure, I tripled logo growth, doubled revenue, and positioned the company for a successful Webflow acquisition. SparkPost → MessageBird (2020). As Global Head of Marketing / CMO, I led GTM across NA, Europe, and APAC. I built the SparkPost brand from the ground up and drove the developer-led and partnership motion that powered the exit. Fountain. As VP of Marketing reporting to the CEO, I led GTM that supported a $180M Series C, also overseeing partnerships, pricing/packaging, and RevOps. I have a RevOps background and am equally fluent in pipeline math as well as brand narrative. I've also scaled ABM and developer growth programs in both technical buyer messaging and executive storytelling. I thrive at companies where marketing is a category-defining function, not a lead factory. I also write about the CMO-to-CRO transition and AI GTM at cmo2cro.substack.com. Open to advisory and board roles in B2B SaaS, AI, MarTech, and developer/infrastructure platforms, and to conversations about fractional CMO/CRO opportunities where marketing operates as a category-shaping revenue function.
Expertise
Experience
Fractional Chief Marketing Officer
Aug 2026 – Present
Humanly.io · Remote
Leading enterprise-wide marketing strategy and operating model assessment to align organizational structure with H2 2026 revenue objectives.
- Developed integrated GTM strategy spanning demand gen, content, PR, and AI visibility.
- Established executive-level performance infrastructure including HubSpot/Notion reporting and KPI scorecards.
- Optimized MarTech stack and vendor spend to reallocate resources to high-impact growth priorities.
Fractional Chief Marketing Officer
Jun 2025 – May 2026
Intelity · Remote
Recruited to lead enterprise brand transformation and GTM modernization for a hospitality technology platform.
- Led company-wide positioning evolution to align AI capabilities with enterprise priorities.
- Built integrated marketing strategy connecting investment directly to pipeline outcomes.
CMO & CRO
Jan 2022 – Apr 2024
Intellimize (acquired by Webflow) · San Mateo, CA
Led both marketing and revenue organizations during a critical growth stage leading to acquisition.
- Doubled average contract value (ACV) and tripled new logo acquisition.
- Repositioned the company around AI-powered website optimization.
- Unified brand, product marketing, demand gen, and SDR functions under a single revenue strategy.
VP of Marketing
May 2020 – Oct 2021
Fountain · San Francisco, CA
Positioned Fountain as a category leader in frontline workforce automation.
- Drove 6x revenue growth
- Rebuilt the marketing department from near-zero to support N. America and EMEA GTM
- Defined enterprise value propositions that won against legacy incumbents
VP of Growth to CMO
Feb 2015 – May 2020
SparkPost (acquired by MessageBird) · San Francisco, CA
Led evolution from infrastructure provider to strategic enterprise platform.
- Quadrupled cloud product revenue
- Built product marketing, ABM, and an enterprise demand engine from scratch.
- Supported a successful acquisition by MessageBird
Education
- Not Specified · Not Specified, Marketing/Business Operations
What I'm looking for
notes: Interested in high-growth companies requiring category creation, brand transformation, or GTM scaling. work mode: Remote industries: Enterprise SaaS, AI, Workforce Tech role types: Chief Marketing Officer, Fractional CMO, VP of Marketing