Michael Bluestein
Marina del Rey, CA, United States0
Head of Sales at Whippy
Enterprise sales and partnerships leader with 11+ years closing complex deals across AI, SaaS, APIs, and insurtech. First sales hire at Sure and REIN, helping scale Sure to $50M+ ARR and a $100M Series C, then building REIN from $0 to $5M+ ARR.
AI Fluency
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Experience
Head of Sales
Whippy AIJun 2025 — Dec 2025 · Los Angeles, California, United States
Led the sales team to 130% of plan and 50% ARR growth, closing $400K to $500K in new ARR per month and lifting demo-to-close conversion to 21%. Built and managed an 8-person SDR and AE team across outbound, pipeline, forecasting, and deal execution. Ran technical discovery and enterprise AI deployments with Product and Engineering on integrations.
Vice President of Sales
REINMar 2024 — Jun 2025 · Los Angeles, California, United States
Employee #4 and first commercial hire, built the enterprise sales motion for an API-first embedded insurance platform from zero. Grew revenue to $5M+ ARR across accounts including Costco, Nationwide, Liberty Mutual, and Rocket Companies. Improved attach rates 40% and partner revenue 17%, and negotiated multi-year agreements worth $750K+ in annual revenue per account.
Senior Manager, Sales & Partnerships
Sure, IncOct 2017 — Dec 2023 · Santa Monica, California, United States
Owned the commercial P&L and drove 20-25% QoQ revenue growth across enterprise and platform partnerships, helping scale Sure to $50M+ ARR, 250+ employees, and a $100M Series C. Launched new products and distribution verticals that produced $3M in first-year ARR. Served as executive sponsor for major enterprise, platform, and carrier accounts and built a 30-person organization.
BloomNation
Feb 2016 — Oct 2017 · 1 yr 8 mos
Head of Sales Development
Jul 2017 — Oct 2017 · Santa Monica, CA
Trained and coached eight SDRs, and the team reached 186% of quota in Q3 2017. Optimized sales processes with data-driven analysis, increasing revenue 25% QoQ. Used competitor research and customer insight to sharpen positioning, pricing, and sales materials.
Senior Account Executive
Feb 2017 — Jun 2017 · Santa Monica, CA
Won $2.2M in new revenue in the first half of 2017, hitting 120% of quota in Q1 and 106% in Q2. Top-performing rep in Q1 and second-highest revenue in Q2.
Sales Development Representative
Feb 2016 — Aug 2016 · Santa Monica, CA
Produced $2.6M in new business for AEs over six months. Top-performing SDR in Q1, Q2, and Q3 2016, hitting 150%+ of quota each month.
Education
San Diego State University
Bachelor of Science - BS in Marketing
University of Oxford
Marketing and Political Science
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Skills
Microsoft OfficeSalesforce.comAX DynamicsMicrosoft PublisherMicrosoft AccessVisioSilverpop EngageSocial Media MarketingMarketing StrategyCompetitive AnalysisProduct MarketingSocial MediaEmail MarketingBusiness StrategyBusiness AnalysisMobile Devices