Head of People Operations

  • Boston, MA
  • Full Time
  • Human Resources
  • Senior Manager/Supervisor

Botkeeper is an automated bookkeeping solution transforming the accounting industry. Named one of America’s fastest growing companies by both Inc. and the Financial Times in 2021, we’re building a team that isn’t afraid to push the boundaries of what's possible. Together, we work hard, collaborate constantly, lift one another up, and challenge each other without fear. Following our Series C funding led by Grand Oaks Capital, we’re now scaling to achieve the future of bookkeeping!

Botkeeper is looking for a Head of People Operations!

Position Overview

As we continue to level-up our organization, we’re looking for a data driven and people-first leader — an individual who’s “not your parent’s HR leader”, who’s passionate, can partner with the leadership team, plans and implements complex employee growth/engagement/retention strategies, understands how “meaning” matters, and can lead by exemplifying our core values (Go Hard, Continually Improve, Care, and Do What’s Right).

You have a clear track record of leading and scaling People Operations at a progressive, high growth company. You have a high level of EQ and are confident in working with executive leadership, taking great joy in being a positive influence.

You will partner and consult with all functions in the company to build and support their teams. This will involve recruiting and retaining the best talent, providing coaching and team leadership resources, helping to resolve employee relations issues, and managing internal programs that help foster talent from within.

What you have done and enjoy doing:

  • Knowledge and experience in employment law, compensation and benefits, organizational development, people analytics, and employee relations
  • Experience in leading and supporting department-specific and org-wide strategic initiatives, soliciting buy-in, partnering with cross-functional partners, and driving scalable solutions
  • Experience with stakeholder management, program design/management, and change management
  • Provide support and consultation across the organization on the most complex issues, supporting staff, managers and executives in all related areas and regions including: recruitment, performance management compensation and rewards, staff relations, and people development
  • Provide useful data and best practices to help guide decision making, and allow the company to scale effectively and efficiently
  • Be able to communicate at all levels in the company and to support business and cultural evolution
  • Lead by example – exemplifying the Core Values: Go Hard, Continually Improve, Care, and Do What’s Right



  • High tolerance for ambiguity – nimble and comfortable working in a fast paced environment
  • High emotional and social intelligence, as well as exceptional interpersonal and communication skills
  • Holds a relevant degree or equivalent practical experience with proof of HR related qualifications and experience in best practice
  • Experience in leading a People Operations team, ideally in the software industry at a high growth startup ($10-$100M ARR) 
  • Demonstrates an ability to challenge conventional approaches, and a desire to architect new processes and procedures
  • Highly trustworthy, ethical, passionate and altruistic
  • Solution-oriented with strong problem solving and critical thinking skills while exercising sound judgment
  • Able to communicate complex ideas and business concepts in accessible terms.
  • Passion for providing employees with the best possible experience
  • Strength in developing bold, creative solutions to address scaling challenges
  • Strong consultation skills and experience influencing and interacting with leaders
  • Proven analytical capabilities; experience with large datasets and in developing audit reports, metrics, and key insights through various reporting mechanisms

About Botkeeper:

Botkeeper provides bookkeeping to businesses using a powerful combination of skilled accountants and automated data entry through the use of machine learning and AI. Our clients receive 24/7 accounting and support as well as incredible insight into their financials with beautiful dashboards and unlimited reporting. The platform easily integrates with a client’s bank accounts, credit cards, HR system, and POS system, and makes appropriate entries and adjustments to their QuickBooks Online accounts, providing businesses with a 24/7 AI-driven Botkeeper. The company is headquartered in Boston, MA. 

Botkeeper Benefits:

We offer unlimited PTO, competitive compensation and healthcare, remote work, and 12 weeks of parental leave. Additional benefits include our annual company retreat, incredible opportunities for career growth, continued professional education, and collaboration with our team of smart, supportive colleagues.

Equal Employment Opportunity Statement:

Botkeeper is proud to be an Equal Employment Opportunity employer and we encourage all to apply to join our team! We do not discriminate based upon race, religion, color, national origin, sex, sexual orientation, gender identity, age, military or veteran status, disability, or any other applicable characteristics protected by law. If you require reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, please direct your inquiries to accommodations@botkeeper.com.

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