Head of Sales

Sales Leader

Kaizen is hiring its first sales leader. We're looking for a proven SLED leader who's equally excited about being in the weeds with our team and customers as they are about building scalable sales processes and growing the team. The ideal candidate should be excited to collaborate closely with the founders to expand upon an existing playbook and should feel energized by the potential to expand Kaizen across other verticals in government.

This is a hybrid role based out of our New York City HQ. The candidate must reside in New York or be able to commute to New York City to work out of our office at least 3x a week.

You're an experienced, proven sales leader with SLED experience. You've helped teams navigate enterprise, public-sector sales cycles at the local, state, and federal levels. You've led field sales motions for software that requires you to meet customers where they are, building deep trust and developing a deep understanding of government operations. You've built and scaled a sales team. You know how to hire, coach, and retain enterprise sellers who thrive in a fast-paced, mission-driven environment. You're not looking to lead from an ivory tower. You lead by example closing critical deals, rolling up your sleeves, and modeling the behaviors you expect from your team.

Leadership and team building : Recruit, hire, and mentor a team of BDRs, AEs, and RFP specialists selling to various customer segments. Build a high-performance culture defined by accountability, high autonomy / ownership, and proactivity. Establish core processes for pipeline management, forecasting, and sales reporting. Partner with the leadership team on compensation design, territory planning, and quota planning as the company scales.

Improve win rates : Dissect every part of our sales motion (top of funnel outreach, conferences and trade-show presence, pricing proposals, RFPs, procurement, etc.) to identify opportunities to increase conversion and shorten deal cycles. Own and continuously evolve our sales methodologies, demo frameworks, top-of-funnel playbooks, and outbound strategy. This will require frequent collaboration with marketing and design to strategize on top-of-funnel strategies. Spend critical time with customers (in-person and virtual) to refine Kaizen's value proposition and messaging.

Sales infrastructure and enablement : Redesign our sales tech stack, partnering closely with team members to remove friction, and leverage automation and AI to accelerate productivity. Implement scalable CRM processes and team and IC reporting, ensuring data accuracy and actionable insights.

Strategy & planning : Partner with founders and leadership on sales forecasting, territory strategy, and GTM planning. Collaborate cross-functionally with marketing on lead generation, ensuring consistency throughout our sales process. Contribute to Kaizen's long-term vision by spearheading market expansion projects and identifying new geographies, customer segments, and verticals within government. Partner with leadership and design to build and test proofs of concept as part of the expansion strategy.

What you'll bring : 8+ years of experience in software sales, with at least 2 years in a leadership role that involved growing and scaling a team. Depth of expertise and knowledge of selling to public agencies, procurement strategies, and field sales.

Compensation : OTE is $450k - $500k, split 50 / 50.

At Kaizen, we believe that great work starts with taking great care of our people. We're building something meaningful, and that starts with a culture where people genuinely love to work. Here's how we support you - in and out of the workplace :

Comprehensive health coverage : We offer Gold, and Platinum PPO plans through Oxford (United), with 85% of premiums covered for employees on the Platinum plan, with a $0 premium option.

Dental, vision & financial wellness : You're covered with Guardian PPO dental and Beam vision plans - Kaizen pays 99% of premiums for employees and 50% for dependents. We also offer :

• $50 / month toward your commute
• One-time setup stipend (up to $750) for your home or NYC office
• $100 / month for wellness or productivity

Perks that make life better : $250 / year for recreation - because fun matters. $500 / year for professional development - because growth does too. Expensed lunch three days a week when you're in the office. Company-provided laptop.

Time off to recharge : Unlimited PTO. All federal holidays off. A company-wide winter break during the week of Christmas.

At Kaizen, we're building something meaningful, and that starts with a culture where people genuinely love to work. Come build with us.