Head of Sales

Turnkey

$200K — $275K *
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7+ years of sales leadership experience managing AEs and BDRs in mid-market and enterprise sectors.
  • Proven success in building and leading high-performing sales teams in fast-paced environments.
  • Strong coaching abilities with high emotional intelligence to develop talent.
  • Experience in unstructured environments where sales processes are still being established.
  • Comfortable with pipeline management, forecasting, segmentation, and process enhancements.
  • Cross-functional collaboration with Product, Marketing, and Leadership is essential.
  • Driven by autonomy, ownership, and building an effective sales organization from the ground up.

Responsibilities

  • Lead and mentor a team of Account Executives (AEs) and Business Development Representatives (BDRs).
  • Drive consistent sales attainment across mid-market and enterprise segments.
  • Build scalable and repeatable sales processes for organizational growth.
  • Collaborate with leadership to refine segmentation and enhance pipeline maturity.
  • Ensure the quality of the sales pipeline and maintain consistent forecasting discipline.
  • Partner with marketing and product teams to enhance market traction.
  • Foster a culture of accountability, collaboration, and high performance within the sales team.

Benefits

  • Comprehensive benefits package including medical, dental, vision, life, disability, and HSA/FSA options.
  • Paid parental leave for new parents.
  • Unlimited paid time off for a healthy work-life balance.
  • $3,000 annual budget for learning and development, including industry conferences.
  • Opportunities for multiple team offsites each year.
  • Monthly lunch stipend to support employee well-being.
Full Job Description
Your Role

As Head of Sales at Turnkey, you will own the entire sales organization and strategy. Unlike many high-growth companies that choose one motion (velocity-driven outbound OR long-cycle enterprise), you9ll build and scale TWO distinct yet interconnected motions simultaneously: a high-velocity developer/SMB motion with outbound-driven AEs and BDRs, and a complex enterprise motion that requires different reps, different playbooks, and different KPIs.

You9ll partner directly with our CEO and founding team to shape our go-to-market strategy, define our market positioning, and make hard tradeoffs on where we invest sales resources. You9ll be building the systems and processes from the ground up around segmentation, accountability, pipeline health and forecasting.

What You9ll Do
  • Own Sales Strategy & Segmentation: Define how we attack the market. Which verticals do we focus on (e.g., crypto exchanges, fintech platforms, institutional custodians, developer-native companies)? What9s the motion for each? How do we segment our team to win in each? You9ll make these decisions in partnership with leadership, but you own the execution.
  • Build & Scale Two Sales Motions: Lead a team of AEs and BDRs focused on high-velocity, outbound-driven pipeline generation in SMB and mid-market, while simultaneously building a separate enterprise motion for longer-cycle, relationship-based deals. These require different talent, different coaching, different metrics. You9ll ensure both thrive.
  • Establish Accountability & Pipeline Discipline: Create a forecasting cadence, pipeline review process, and accountability system that actually works. You9ll know what each rep owns, what deals are at risk, and why. You9ll drive real insights back to the team on what9s working and what isn9t-and course-correct quickly.
  • Develop Sales Leadership: You9ll hire and coach Sales Managers who sit between you and the reps. Build a bench of leaders who share your philosophy and can scale with the company.
  • Partner on GTM & Product Strategy: Work closely with the CEO, Product, and Marketing to refine our positioning, identify market opportunities, and provide feedback on product-market fit. You9ll bring the voice of the customer and the market into internal strategy conversations.
  • Recruit & Build High-Performing Teams: Source and recruit top talent that fits our culture and market. You9ll set hiring bar, build team composition, and create a place where ambitious people want to work.
  • Drive Predictable Growth: Own the sales number. Build a sales org that scales revenue predictably quarter over quarter, understanding how many reps you need, what productivity looks like, and how to hit plan.

What We9re Looking For
  • Proven track record building sales organizations from the ground up. You9ve scaled a sales team from 0 to 10+ in a high-growth environment. You didn9t inherit a team with existing playbooks; you built them. This is non-negotiable.
  • Experience managing TWO distinct sales motions or segments simultaneously. You9ve either led teams selling to both SMB/mid-market and enterprise, or you9ve managed outbound velocity and inbound/partnership channels in parallel. You understand that different segments need different approaches-and you can coach leaders through both.
  • Deep understanding of developer-first / API-driven / infrastructure sales. You9ve sold infrastructure, APIs, developer tools, or technical SaaS to both developer buyers and enterprise buyers. You know how to avoid treating developers like enterprise customers.
  • Exceptional coaching and people leadership skills. You9ve taken underperformers and either elevated them or moved them on. You know how to hire for potential, not just credentials. You care about rep development, not just quota attainment.
  • Comfort in ambiguity and ownership mentality. You don9t need a 500-slide deck to make decisions. You9re comfortable saying 4we don9t know yet, let9s run an experiment.4 You take ownership of outcomes, even when things are messy.
  • Systems thinker and process builder. You9ve built forecasting systems, pipeline hygiene processes, and accountability mechanisms that scale. You9re not just good at sales-you9re good at building the machinery that makes sales scalable.
  • Strategic partnership with executive leadership. You9re comfortable challenging the CEO when you have data, and being challenged back. You see your role as shaping GTM strategy, not just executing a pre-built plan.
  • You9re based in New York or willing to relocate. You will be in the office full-time and embedded with the team. This role requires in-person partnership with leadership and the sales team.

Style Points
  • Experience in fintech, crypto or security infrastructure
  • You9ve led sales through a significant scale inflection
  • You9ve built a sales org that maintained strong culture and rep retention while scaling quickly.
  • You9ve successfully launched a new vertical, motion, or market segment that materially contributed to growth.
  • You9re plugged into the crypto ecosystem-you follow the market, you know the key players, and you understand where the market is heading.

What We Offer
  • Full benefits, including medical, dental, vision, life, disability, HSA/FSA, 401(k)
  • Paid parental leave
  • Unlimited PTO
  • $3,000/yr learning and development budget for conferences and education
  • Multiple team offsites per year
  • Lunch stipend


Compensation range

$200,000-$275,000 USD

Similar Jobs

More Enterprise Technology Jobs

Find similar Head of Sales jobs: