# Janelle Wolak > Chief of Staff | VP, Strategy & Operations | 9-Figure Exit Location: San Francisco Bay Area, United States Profile: https://flows.cv/janellewolak Strategy + product + ops leader, with a bias for decision and follow-through. I partner with CEOs to cut through the noise, tradeoffs, and competing opinions to find the 2-3 highest-leverage decisions that actually move the business. Then I lead cross-functionally to build the roadmap and execution system that turns those decisions into shipped outcomes at scale. Most recently, at Insight M, I drove a full business model transformation that enabled $82M fundraise and 9-figure acquisition. Before that, I built the product and customer operations org that doubled market share for an enterprise SaaS platform. Before that, I took a startup from concept to first revenue as the fire hire. My edge is that I build systems that are grounded in real customer problems, are driven by data not opinion, and are designed to outlast me. ## Work Experience ### VP, Strategy & Operations and Chief of Staff @ Insight M Jan 2023 – Present | San Francisco Bay Area Served as the CEO's operating partner across all core functions - driving company-wide planning, resource allocation, and executive decision-making through a period of rapid transformation. Managed Business Operations and Product. • Led a full services-to-SaaS transformation - operating model restructure, change management, workforce planning, product operations - cutting burn ~56%, expanding margins +26pp and revenue 1.8x, and delivering the subscription platform that became a key value driver in the acquisition. • Ran fundraising and M&A end-to-end - diligence, stakeholder coordination, and integration planning across $82M raised (BlackRock and Morgan Stanley 1GT) and a nine-figure acquisition by Zeitview. • Rebuilt the company-wide operating infrastructure - revenue operations, OKRs and accountability systems, executive reporting - taking forecast accuracy from unreliable to a weekly discipline and reducing time to customer value from days to next-day. ### Chief of Staff @ Insight M Jan 2022 – Jan 2023 | San Francisco Bay Area ### Director, Product Strategy and Operations @ JetInsight Jan 2021 – Jan 2022 | San Francisco Bay Area Led cross-functional operations across product, engineering, and customer success & support for an enterprise platform serving 200+ operators. Managed a product team while owning the full operational infrastructure across four functions. • Built the full operational infrastructure from scratch - Voice of Customer program, prioritization framework, delivery process - cutting support escalations by 50%, time from customer request to product decision from months to one week, and delivering near-perfect gross retention. • Identified two untapped revenue opportunities, built the products to capture them, and scaled transaction volume nearly 5x while doubling market share. ### Head of Product @ JetInsight Jan 2020 – Jan 2021 | San Francisco Bay Area ### Product Manager @ JetInsight Jan 2019 – Jan 2020 | San Francisco Bay Area ### Founding Product Manager @ Blis Jan 2018 – Jan 2019 | Lafayette, California As first hire, built the 0→1 product and operating model from concept to first revenue for an early-stage talent marketplace that enables companies to find and hire freelance content creators. Drove first revenue, staffing 30+ creators for a flagship program. ### Product Manager (Innovation / New Product Incubation) @ Wells Fargo Jan 2017 – Jan 2018 | San Francisco Bay Area Led 0→1 incubation from concept to executive narrative, prototype, and pilot plan for next-gen digital banking. Supported close of Hotels.com co-brand credit card partnership by designing the customer experience prototype that anchored the GTM narrative. ### Design Strategist @ MKThink Jan 2016 – Jan 2017 | San Francisco, CA ### Designer @ Hayes Group Architects Inc. Jan 2015 – Jan 2016 | Redwood City, CA ## Education ### Bachelor of Science (B.S.) in Architectural Design & Engineering, Minor in Human Biology Stanford University ### High School Diploma Castilleja School ## Contact & Social - LinkedIn: https://linkedin.com/in/janelle-wolak --- Source: https://flows.cv/janellewolak JSON Resume: https://flows.cv/janellewolak/resume.json Last updated: 2026-04-05