Craig S.

Positioning, copy, and 0-to-1 GtM strategy for B2B/Enterprise Tech

I build go-to-market strategies for early-stage B2B SaaS selling complex products to enterprise buyers. I focus on pipeline generation, repeatable sales processes, and revenue, not vanity metrics. WHAT I DO: I work with founders to define positioning, build demand generation systems, optimize sales funnels, and create repeatable GTM. I do both strategy AND hands-on execution. Core expertise: GTM strategy for early-stage products • Positioning and messaging • ICP definition • Demand generation (outbound, LinkedIn, partnerships, content) • Sales funnel design • Founder-led marketing • Customer discovery • CRM optimization • Sales process design • Pricing strategy • Product-market fit validation WHO I WORK WITH: Early-stage SaaS ($0–$5M ARR) selling to enterprise buyers, technical decision-makers, executives, or regulated industries with long sales cycles and complex products. DOMAIN EXPERTISE: Deep experience in cybersecurity/infrastructure, PropTech, professional services, AI products, workflow automation, and compliance platforms. I understand how technical and executive buyers evaluate solutions and how to position products that don't fit easy categories. RECENT WORK: Head of Marketing, Tailorbird (Series A PropTech/AI). Built marketing function from zero. Repositioned product, conducted customer discovery, created outbound playbooks, launched demand generation across channels, and worked with founder on positioning. Results: doubled ARR in 12 months, 5x CAC:CLV, $100 CPL, 1.5–2% demo booking rate from cold outreach. Fractional CMO, 14+ years. Positioned complex technical products for enterprise buyers. Built demand generation systems, optimized LinkedIn (CPL reduced $1,000+ to $110), diagnosed structural sales/marketing misalignment (diagnosis validated when client reorganized 3 months later), designed sales processes. WHY I'M DIFFERENT: I optimize for pipeline and revenue, not activity. I focus on positioning clarity first, then execution. I work hands-on AND think strategically. I'm honest about gaps and clear about what works. MY APPROACH: 1. Discovery: Interview customers, prospects, sales. Understand real buyer and decision journey. 2. Tight ICP: Not "everyone." Which buyer has most acute pain? 3. Repeatable GTM: Outbound campaigns, content, partnerships, founder positioning. Test, cut, scale. 4. Measure what matters: Pipeline, conversion, CAC, revenue. Not impressions or vanity MQLs. 5. Iterate: Daily/weekly/monthly reviews. What works? What doesn't? Double down or cut? WHAT I'M LOOKING FOR: Ongoing fractional work or project-based engagements with founders. I'm interested in hard problems, including undefined categories, conservative buyers, complex products, long sales cycles, and building from nothing. ENGAGEMENT OPTIONS: I offer flexible structures, including monthly retainer, hourly, fixed project, or hybrid. I'm always happy to trial to validate fit. • Monthly fractional retainer (ongoing strategic guidance + execution) • Project-based (4–12 week GTM strategy and build sprint) • Hourly (flexible as needed) • Hybrid (retainer + project work) I'm happy to start with a 2-week trial or smaller project to validate fit before committing to longer engagement. BOTTOM LINE: If you're building something ambitious, especially in complex B2B markets with conservative buyers or undefined categories, and you need someone to help position it, generate real pipeline, and build repeatable GTM systems, let's talk. I work directly with founders and similar roles. I do both strategy and execution. I think in terms of metrics that matter (pipeline, conversion, revenue). I'm honest about what will work and what won't. Ready to start immediately.