Paul S.
Fractional Sales Leader | GTM Strategy & Playbooks for B2B SaaS/MSP
After helping build the land and expand playbook that scaled Alteryx from $12M to unicorn status (employee #170, founding member of strategic team) and leading strategic revenue initiatives at Quest Software (through its Dell acquisition), I made an intentional pivot: take the enterprise-grade frameworks that work at scale and install them in growth-stage teams who can't afford dedicated enablement. I spent the last period traveling the country (yes, in an RV with my dog), coaching founders and sales leaders, and refining what moves the needle when you're stuck in the messy middle between founder-led sales and scalable revenue operations. Now I help B2B SaaS, MSP, and data platform teams ($500K-$20M ARR) build the systems their sellers need to succeed. Not strategy decks. Working systems: expansion playbooks, qualification frameworks, champion building methodologies, deal coaching - the stuff I designed at Alteryx, simplified for teams of 1-10 sellers who need enterprise discipline without enterprise overhead. Track Record 75%+ pilot-to-enterprise conversion rate (Alteryx/Quest Software methodology) $25M+ individual deals closed using these frameworks 100%+ quota attainment leveraging expansion systems year over year 15+ years enterprise B2B sales and leadership What I Deliver Core Services * Expansion Playbook Implementation * Complete pilot-to-enterprise conversion system * Champion recruitment & arming frameworks (not just identification) * Value quantification methodology (turn features into business cases) * Deal qualification scorecards (know what's real vs wishful thinking) * Mutual action plans & proof loops * Live team training + 30-60 day support Sales Playbook Build * ICP definitions with account tiering * Buyer persona matrix (4-6 personas with pain points, KPIs, objections) * Sales question library (discovery through close) * Objection handling by stage * Call programs & follow-up cadences * Manager coaching frameworks Fractional Sales Coaching * Weekly deal reviews using proven frameworks * 1-on-1 rep skill development (discovery, negotiation, champion building) * Pipeline reviews & forecast accuracy improvement * "Our proposal, our timeline" collaborative language training * Long-game deal structuring (plant seeds for 12 months out) 7-Day GTM Diagnostic * Complete sales motion health check * Findings report with prioritized backlog * 30-60-90 day roadmap with quick wins * Risk map & action plan with owners Who I Work With You're an ideal fit if: * B2B SaaS, MSP/MSSP, or Data/AI platform * $500K - $20M revenue * 2-10 sellers (AEs, AMs, BDRs) * Land-and-expand motion (pilots, POCs, tiered products) * Founder transitioning out of sales OR first VP Sales hire Common pain points I solve: * Pilots go well but don't expand (conversion <30%) * Reps say different things on the same call * Pipeline full of stalled deals with no clear next step * CRM is a mess, forecast is guesswork * Expansion revenue is accidental, not systematic * Hired sellers but haven't built systems t need to succeed We're NOT a fit if: * No CRM or unwilling to use one * Purely transactional/e-commerce models * Enterprise deals >$250K ACV (too long for sprint model) * Looking for ongoing managed service (I'm project-based) * Need marketing/demand gen/RevOps technical work What You Get * Not strategy decks. Working documents: * Signal Discovery Guides (15-20 questions by expansion stage) * Value Hypothesis Cards (1-page business case builder) * Champion Brief Templates (recruit & arm internal advocates) * Deal Physics Scorecards (qualification with red/yellow/green indicators) * Mutual Action Plan Templates (next steps tracker) * Indecision Playcards (what to do when deals stall) * Manager Coaching Frameworks (coach to standards, not gut feel) Core Philosophy: * Long-game mindset - Plant seeds for deals 12 months out * Win-win foundation - Both sides feel good about the outcome * Genuine curiosity - Make getting to know them real * Collaborative selling - "Our" language, not "my pitch vs your objections" * Own your word - Commitments matter * Champion building (really) - Not just identification, actual recruitment and arming I build sales systems and coach teams to execute
Earnings and projects
Last 6 months ÷ 6
Last 6 months: $7.9k
Billed in all: $26,560$27k
$4k in the last 6 months
Earnings, last 30 days
Skill rankings: Top 4% in Sales Copy
Ranked by MRR among everyone on Upwork with the skill.
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