Senior Manager, Business Recruiting

About the role:

Headway is hiring a Senior Manager, Business Recruiting to lead our Go-To-Market (Sales, Marketing, RevOps) and G&A recruiting teams. This is a highly visible leadership role responsible for evolving Business Recruiting to meet the growing hiring needs through strategic, data-driven hiring at scale.

You will lead and develop a team of recruiters across a mixed hiring portfolio, balancing high-volume GTM hiring with highly competitive, high-touch G&A roles. You’ll partner closely with executive leaders and HRBPs to translate business goals and headcount plans into executable recruiting strategies, while raising the bar on how the team sources, closes, and operates.

This role blends people leadership, operational excellence, and executive influence. Success requires comfort operating at both the strategic and tactical levels. You’ll set direction, rebuild processes, and ensure consistent execution through others. The best person for this role is both a strong people leader and a visionary in recruiting. 

You will

• Lead and mentor a team of Business recruiters (GTM + G&A); fostering a culture of excellence
• Partner closely with C-suite and senior leaders across GTM and G&A to design hiring strategies aligned to business priorities, headcount plans, and market realities
• Translate complex hiring goals into milestone-driven execution plans
• Use data to proactively diagnose hiring challenges in close partnership with recruiters
• Elevate sourcing and closing capability across the team, especially in competitive GTM markets with candidates managing multiple offers
• Serve as a trusted advisor to executives, communicating tradeoffs clearly, delivering difficult feedback when needed, and influencing decisions with structured recommendations
• Continuously improve the candidate and hiring manager experience, ensuring Headway’s business hiring process is efficient and aligned with our values

You’d be a great fit if you…

• Bring 10+ years of recruiting experience, with 6+ years in people management
• Have deep experience across Business Recruiting, including GTM (Sales, Marketing, RevOps) and G&A hiring, with exposure to both high-volume and high-touch searches
• Operate as a true business partner, grounding your strategies and recommendations in data, market insight, and business context
• Are an operationally excellent leader who can move teams from reactive execution to proactive strategy
• Are comfortable working directly with C-suite and senior leaders, navigating competing priorities and influencing decisions with clarity and conviction
• Communicate with clarity and executive presence, tailoring your message to different audiences and navigating sensitive conversations with maturity
• Bring a bias for action and results, prioritizing ruthlessly and maintaining urgency without sacrificing quality or team health

Compensation and Benefits:

The expected base pay range for this position is $144,000 - $225,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development