Regional Director, Mid-Market

Factory

$130K — $180K *
Information Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 6+ years in B2B SaaS sales; 2+ years in a quota-carrying leadership role in Mid-Market with complex sales cycles.
  • Proven track record of exceeding personal quota before moving into a managerial role.
  • Experience selling technical products to engineering teams (strong preference for developer tools, DevOps, or platform software).
  • Demonstrated ability to build and scale teams or offices, actively involved in hiring and onboarding.
  • Strong skills in forecasting, pipeline management, and sales processes; data-driven approach.
  • Strong coaching abilities with technical aptitude to enhance reps' evaluation and demo skills.

Responsibilities

  • Own and drive Mid-Market team revenue while exceeding sales targets.
  • Lead and develop a team of 6-8 Mid-Market Account Executives.
  • Coach throughout the entire Mid-Market sales process from pipeline generation to closing.
  • Maintain an accurate weekly sales forecast and healthy sales pipeline.
  • Refine and build the playbook for outbound sales and improve conversion rates.
  • Establish sales culture and routines in the San Francisco and New York City offices.
  • Collaborate with multiple departments to customize solutions and drive sales growth.

Benefits

  • Opportunity to lead and shape a pioneering sales team in a dynamic organization.
  • Direct involvement in building and scaling key office cultures in major cities.
  • Significant autonomy in developing effective sales strategies and training.
  • Interaction with C-suite personnel and engineering leaders to create tailored solutions.
Full Job Description
You will lead one of the pioneer Mid-Market sales teams from the front. You own a team of Account Executives selling to engineering organizations under 1,500 employees, and you carry the number for the region. You will also anchor and help scale our San Francisco & New York City offices, hiring, ramping, and building the culture of the first and second GTM hubs.

You will lead a team of Mid-Market Account Executives who run technical, multi-stakeholder sales cycles into engineering organizations, selling Factory's Droids to CIOs, CTOs, engineering leaders, and procurement. This is a player-coach role for someone who has carried a bag, hit the number, and then built the team that does it repeatedly. You coach deals daily, run a tight forecast, and raise the bar on talent.

What You'll Do
  • Own Mid-Market team revenue. Hit and exceed quarterly new-logo and expansion targets with the majority of reps hitting quota.
  • Lead a team of 6-8 Mid-Market AEs. Hire, onboard, ramp, coach, and performance-manage.
  • Coach end-to-end Mid-Market cycles: pipeline generation, technical evaluations and POCs, multi-stakeholder navigation across CIOs, CTOs, engineering leaders, and procurement, commercial negotiation, and close.
  • Run an accurate weekly forecast and a healthy, inspected pipeline. No surprises.
  • Help build/scale the playbook: refine the outbound motion, POC-to-close conversion, and the path from self-serve to enterprise.
  • Anchor the SF & NYC offices. Establish the in-person sales culture, rituals, and bar for the first and second hubs.
  • Partner with the CEO, Sales Engineering, Product, Engineering, Marketing, and RevOps to customize solutions, drive expansion and renewal, and compound pipeline.
  • Model the work. Get in deals, talk to engineering leaders, and stay fluent in how Factory creates value.


What You'll Bring
  • 6+ years in B2B SaaS sales, with 2+ years leading a quota-carrying team as a first-line manager, ideally in Mid-Market with complex, multi-stakeholder cycles.
  • A track record of personally carrying and exceeding quota before moving into leadership.
  • Proven success selling technical products to engineering buyers (developer tools, DevOps, infrastructure, or platform software strongly preferred).
  • Experience building or scaling a team or office from an early stage. You have hired and ramped reps, not just inherited them.
  • Command of forecasting, pipeline inspection, and sales process. You run on data.
  • A coaching instinct and the technical aptitude to coach evaluations and demos for DevEx and engineering buyers. Your reps get better because of you.


Nice to Have
  • Experience selling AI or agentic products to technical buyers.
  • Early-stage or founding GTM experience (Series A/B).
  • An existing network among mid-market engineering leaders.
  • Willingness to work onsite 5 days/week in SF or NYC.

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