Head Of Sales

Outtake

$160K — $200K *
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years in enterprise B2B SaaS sales, including 5 years in direct leadership
  • Proven success in closing six- and seven-figure deals
  • Experience selling into security, risk, or adjacent enterprise tech
  • Ability to build and develop high-performing sales teams
  • Technical fluency to communicate AI capabilities
  • Strong hunter mentality with a track record of creating pipelines
  • Presence in the Brooklyn office required weekly

Responsibilities

  • Own and exceed revenue targets for the US territory
  • Hire and lead a team of Enterprise Account Executives
  • Develop and execute a strategic territory plan
  • Engage with security executives at major companies
  • Collaborate with Product, Marketing, and Customer Success teams
  • Establish operational practices for pipeline and forecast management
  • Represent Outtake at industry events and forums
  • Provide strategic field insights to influence product roadmap

Benefits

  • 100% company-paid medical, dental, and vision insurance
  • Flexible PTO to manage personal time away
  • Collaborative work environment in a waterfront Brooklyn office
  • Regular annual retreats and in-person events for team bonding
Full Job Description
The Role

As Head of Sales, you'll lead and grow Outtake's revenue presence across the US. You'll build and develop a team of AEs, and go deep with the CISOs, Threat Intel leaders, and brand protection executives who will define this market. You'll report directly to the VP, Global Sales and operate as a key voice shaping Outtake's go-to-market strategy.

At Outtake we are the company where AI Enabled Enterprise selling is innovated, taught, and practiced. Your successful programs and processes from the past are stepping off points to a more efficient AI driven sales process that will drive impactful customer outcomes.

What You'll Do
  • Drive the number: Own and exceed quarterly and annual revenue targets for the US territory
  • Lead from the front: Hiring, developing and leading a team of Enterprise Account Executives across the US
  • Build territory strategy: Develop and execute a territory plan that balances pipeline coverage, strategic accounts, and vertical focus
  • Command the executive room: Engage directly with CISOs, Threat Intelligence leads, fraud teams, and brand protection stakeholders at F500 and Global 2000 companies
  • Drive expansion: Partner with Product, Marketing, and Customer Success to ensure customers achieve ROI and expand their footprint over time
  • Run a tight operation: Build a cross-functional operating cadence around pipeline, forecasting, deal reviews, and regional go-to-market execution
  • Be a regional presence: Actively represent Outtake in the US cybersecurity and DRP community-at conferences, customer events, and key industry forums
  • Shape the category: Feed strategic insights from the field directly into product roadmap and positioning conversations


What You'll Need to Bring
  • 10+ years in enterprise B2B SaaS sales, with at least 5 years in a direct leadership role
  • Proven track record closing six- and seven-figure deals with complex, multi-stakeholder enterprise buying cycles
  • Background selling into security, risk, or adjacent enterprise technology. Comfort navigating CISO, SOC, and Threat Intel buyers is a strong advantage
  • Experience building and developing sales teams from early-stage; you know how to hire, ramp, and retain high-performers
  • Technical fluency sufficient to lead credible conversations with CISOs, Threat Intel teams, and brand protection leaders, and translate complex AI-driven capabilities into business value
  • Hunter DNA. You create pipelines, experiment with new approaches, and push through ambiguity
  • Presence in our Brooklyn office is required weekly
  • Strong operational discipline: accurate forecasting, pipeline management, and structured deal review cadences
Life at Outtake
  • Office: For those in NY, we are an in-person team (5 days a week, with flexibility as needed) working out of a stunning waterfront office in Brooklyn. Collaboration, speed, and clarity matter.
  • Health: 100% company-paid medical, dental, and vision for employees.
  • Time Away: Flexible PTO. We trust adults to manage energy, not clock time.
  • Culture & Team: Annual company retreats and regular in-person events.

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