Vice President of Sales

October 31, 2026

About Betterworks

Betterworks is HR software to align, develop, and activate your workforce for business growth. Organizations are able to replace outdated, ineffective, universally loathed annual review processes with powerful Continuous Performance Management programs that help managers be better at the conversations, coaching, and development necessary to inspire and motivate the entire workforce to achieve an organization's top priorities today and be ready for tomorrow's challenges.

The Role

Betterworks is hiring a VP, Enterprise Sales to lead an established team of 6-8 Enterprise Account Executives driving new business across North America. This is a senior first-line sales leadership role: you will own team performance, forecasting, and pipeline execution day to day, while also serving as one of the company's most influential voices on what it takes to win in the enterprise segment.

Beyond team leadership, this role carries high strategic scope. You will work directly with Marketing, Product, and the Executive team to define the positioning, content, product capabilities, and executive engagement needed to compete and win against enterprise HR-tech incumbents. You are as comfortable running a forecast call as you are in a product roadmap review or an exec sponsor meeting with a Fortune 500 prospect.

This is a US remote opportunity!

What You'll Do

Lead the team: Own every part of leading a six to eight-person Enterprise AE team selling net-new business into large, complex organizations across North America. Forecasting, pipeline coverage, and quota attainment.
Coach and develop: Coach reps on complex, multi-stakeholder enterprise sales cycles: deal strategy, multi-threading, executive engagement, and navigating procurement.
Build the bench: Recruit, ramp, and retain top enterprise sales talent as the team scales; build a strong performance culture and clear career paths for a mature, established team.
Help shape GTM strategy: Serve as a primary voice from the field into Marketing and Product on what enterprise buyers need to say yes, competitive positioning, messaging, content, and pricing/packaging for the segment.
Influence the roadmap: Partner directly with Product leadership to prioritize the roadmap based on what is winning and losing enterprise deals; represent the voice of the enterprise buyer in planning.
Drive exec engagement: Act as an executive sponsor on strategic opportunities, engaging directly with C-suite and senior HR/People leaders at target accounts alongside your team.
Cross-functional alignment: Partner with RevOps, Customer Success, Professional Services, Legal, and Solutions Engineering to remove friction from the enterprise sales motion and improve win rates and cycle times.
Report and forecast: Deliver accurate forecasts and clear, data-backed reporting on pipeline health, win/loss trends, and competitive dynamics to the executive team and board as needed.

What You'll Bring

10+ years in enterprise SaaS sales, including 4+ years managing quota-carrying Enterprise Account Executives selling complex, multi-stakeholder SaaS deals, ideally in HR tech, HCM, or adjacent enterprise software.
Proven quota attainment: A track record of consistently hitting or exceeding team quota, with strong command of enterprise sales methodology (e.g., MEDDIC, Challenger, Command of the Message, or similar).
HR buyer experience: Direct experience selling into HR and People leaders (CHRO, VP People, Head of Talent) is required, you understand how HR buyers evaluate, budget for, and champion software internally.
Startup experience: True startup experience is a must-have, you've operated in a fast-paced, resource-constrained environment and know how to build process, not just execute against one that already exists.
Cross-functional influence: A demonstrated ability to influence Marketing and Product leadership - you've helped shape messaging, competitive strategy, and roadmap priorities based on field insight, not just executed against them.
Executive presence: Comfortable and credible in front of C-suite and senior HR/People leaders as an executive sponsor on strategic deals.
Player-coach mentality: A leader who invests in coaching, gives direct feedback, and has built or scaled high-performing enterprise teams.

Why Betterworks

You'll join at a pivotal moment for the Enterprise segment, with a relatively new, but fully ramped team closing significant Enterprise logos and a clear mandate to shape not just how we sell, but what we sell and how we position it. This role sits close to the executive team and has a real, visible hand in company strategy, not just quota attainment.

What We All Do

All employees share the responsibility of being aware of information security risks and adhering to information security policies and procedures.

All employees are required to participate in information security awareness and training programs.

All employees are responsible for handling data in accordance with data classification and handling guidelines. Employees should be aware of the sensitivity of the data they interact with and follow appropriate security measures.

All employees have a responsibility for reporting information security incidents in accordance with information security policies and procedures.

What Makes Betterworks Unique

At Betterworks, we prioritize our people. In that spirit, we've put together a great benefits program to support our employees' health and wellness that includes the following:

" Leadership: CEO Doug Dennerline is truly a mission-driven leader. He has been a sales leader for over 25 years and has a direct impact on the work people do every day.

" Funding: $129 million, Serious B with top tier investors, including Kleiners Perkins, Emergence Capital, and 8VC.

" Board of Directors: Includes iconic executive John Doerr (introduced OKRs to Google), Bruce Felt (Founder of Renaissance Software and a servant leader to various private and public companies), Bing Gordon (Technology Venture Capitalist and history of serving on several high-profile Boards of Directors including Amazon, Duolingo, and Zynga), Jason Green (Founder Emergence Capital and Greenbridge Foundation) and Gaby Toledano (seasoned executive with nearly three decades of strategic HR and operations leadership at premier enterprise and consumer organizations).

" Perks: 100% paid Medical/Vision/Dental for employees, Flexible time off, Parental Paid Leave policy, monthly internet stipend, flex days, and more.

" Product: Selected by Lighthouse Research & Advisory and UNLEASH America, Betterworks has officially been named a 2026 HR Tech Award winner for Best Comprehensive Talent Management Solution. Also, Betterworks wins Newsweek's AI Impact Award for Best Outcomes in HR, 2025. Last, Betterworks was recognized on TIME's list of America's Top WorkTech Companies 2026.

" Mission Driven: Our mission is to provide the expertise and technology that companies need to inspire, develop, and activate their workforce to meet today's goals and be ready for tomorrow's challenges.

We are an equal-opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We are committed to an inclusive and diverse BetterWorks. We believe that different perspectives lead to better ideas, and better ideas allow us to better understand the needs and interests of our diverse, global BetterWorks Community. We welcome people of different backgrounds, experiences, abilities, and perspectives and are an equal-opportunity employer.

Remote

Skills:
Artificial Intelligence (AI), Budgeting, Business Growth, Business Strategy, Coaching, Competitive Analysis/Strategy, Cross-Functional, Direct Sales, Enterprise Applications, Enterprise Sales, Establish Priorities, Exceeded Sales Goal, Field Marketing, Financial Trend Analysis, Forecasting, Fortune 500 Customers, Funding, Human Resources Software, Human Resources Strategy, Information/Data Security (InfoSec), Leadership, Legal, Marketing, Meet Sales Quota, Microsoft Bing Search Engine, Multithreaded Programming, Needs Assessment, Performance Management, Pricing, Product Planning, Product Positioning, Product Reviews, Professional Services, Purchasing/Procurement, Sales, Sales Cycle, Sales Management, Servant leadership, Software as a Service (SaaS), Startup, Talent Management, Team Lead/Manager, Training Program, Venture Capital

BetterWorks Systems Inc

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