Michael Walker, Sales Expert in New York, NY, United States
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Michael Walker

Sales Expert

New York, NY, United States

Toptal member since March 25, 2026

Bio

Michael is a hands-on revenue and GTM leader who loves to bring in clients with 15+ years of experience building and scaling consultative enterprise sales motions across data analytics and AI-driven services/SaaS in the Americas and EMEA. He creates repeatable GTM systems to accelerate bookings, increase ACV, shorten cycles, and improve unit economics. His background includes ICP/ABM, pricing and packaging, MEDDPICC qualification, pipeline and forecast discipline, and operating rhythms.

Expertise

  • Asana
  • B2B
  • HubSpot CRM
  • Revenue Growth
  • SaaS Sales
  • Sales Enablement
  • Salesforce Sales Cloud
  • Strategy

Work Experience

CEO

2024 - PRESENT
NavOut AI
  • Founded an AI startup building recommendation models. The system was built for executive-to-operational product and engineering teams, optimizing eCommerce and marketplace conversion rates.
  • Owned product vision, roadmap, and GTM strategy. Planned and led Agile delivery from ideation to deployment and established KPIs to measure solution impact.
  • Ran executive reporting directly with the board on roadmap, GTM priorities, and KPI progress. Oversaw P&L management and partner negotiations.
  • Branched into consulting other startups on GTM, helping close deals, and advising on what team members to bring on.

VP of Sales

2020 - 2023
Blue Orange
  • Sold data/AI transformation engagements and productized analytics offerings (new line items and upsells) into enterprise accounts.
  • Owned revenue growth from $4.5 million to nearly $20 million and delivered 113% of 2022 year-end goals across enterprise, mid-market, and SMB. Typical enterprise deal size ranged form $50,000 to $250,000 with 3 – 5 stakeholders.
  • Designed and scaled the first successful sales program from 3 AEs/SDRs to a multi-department 20+ person organization, leading 8 quota-carrying AEs and CSMs plus 2 direct leaders with net-positive productivity in less than 5 months.
  • Increased qualified pipeline from $2 million to $30 million by aligning outbound sales and marketing initiatives and implementing ABM.
  • Reduced customer CoA by 35% through process efficiencies. Launched 3 sellable line items that doubled initial contract values and upsold 75% of existing accounts within 6 months to increase LTV.

Director of Enterprise Sales

2020 - 2021
quantilope
  • Refined and executed Series B US scale-up strategy while aligning the international sales organization. Created territories, KPI reporting, and commission structures. Reported to the global VP of sales and CCO.
  • Managed an ARR quota of $9.6 million with 2 managers and 17 AEs. Achieved 103% quota. Increased ACV by 40% by coaching a consultative solution.
  • Implemented MEDDPICC, reducing average sales cycle from 9 months to 4.5 months and growing qualified pipeline 2.8x.
  • Modernized workflows to cut redundancies by 20% and scaled headcount by 2x through strategic hiring of 25 team members.
  • Owned executive forecasting and KPI reporting cadence with CRO and VP leadership to drive pipeline hygiene, deal inspection, and predictable attainment.

Director of Enterprise Sales

2018 - 2020
SurveyMonkey
  • Led US enterprise growth through acquisitions. Built a CXM sales strategy to unify 3 products and drive cross-sell adoption across new and existing customers.
  • Led 2 AE teams to 98% – 130% quarterly quota attainment, supporting global ARR growth from $4 million to $18 million.
  • Increased ACV 2.8x via Challenger-based consultative selling and pricing initiatives adopted globally. Built ABM motion, generating a qualified pipeline averaging 3x quota.
  • Built and led a cross-company POD team. Increased ACV 2.2x and signed the largest deal of 2020. Partnered with sales enablement to produce training rolled out to 400+ sellers.
  • Owned executive forecasting and KPI reporting cadence with CRO and VP leadership through acquisition integration and product unification.

Skills

Competencies

B2B

Roles

Sales Enablement

Other

HubSpot CRM, Revenue Growth, Strategy, SaaS Sales, Salesforce Sales Cloud, Asana, Notion, Figma, Sales

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