Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.
Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves.
Five9 is rewiring the contact center industry with AI that actually works — and we need a proven enterprise sales leader to own a high-growth territory, build an elite team of new-logo hunters, and put up numbers that turn heads. If you've built winning teams, closed complex deals at the C-suite, and thrive in the messy, high-stakes world of enterprise software, keep reading.
East Coast – Michigan, Ohio, Indiana, Kentucky, Tennessee, Virginia, West Virginia, DC, Maryland or Delaware
What You’ll Own
- Lead, coach, and push a team of Enterprise Sales Directors to exceed revenue targets — not just hit them.
- Drive new logo acquisition across the region; this is a hunting role and your team's output reflects your intensity.
- Be in the field — at least two customer-facing meetings per rep per month; you close alongside your team, not behind a dashboard.
- Build and execute a regional business plan across direct, channel, and partner motions to stack a healthy, predictable pipeline.
- Own forecast accuracy in Clari — commits mean something on your team; pipeline hygiene is non-negotiable.
- Recruit and develop top sales talent relentlessly — your bench defines your ceiling.
- Represent the region at QBRs with sharp business acumen, clear metrics, and a credible plan forward.
- Sell against and stay ahead of competitors — NiCE CXone, Genesys, and the new AI-native challengers.
What It Takes
- 10+ years of enterprise software sales — you've won at the C-level, in complex multi-stakeholder environments.
- 5+ years leading high-performing SaaS sales teams; you've built cultures, not just carried a number.
- Deep fluency in SaaS/cloud platforms — you can demo, position, and defend the value in any room.
- A genuine track record of quota overachievement, not just attainment.
- Contact center and/or AI platform experience is a strong plus — you understand the ecosystem.
- Comfortable with 30%+ travel across the territory; you're energized by customer time, not drained by it.
- Sharp communicator — equally credible in a boardroom and on a Zoom with a skeptical IT director.
- Bachelor's degree required.
Why Five9
We're in a genuinely rare moment — AI is transforming the contact center, and Five9 is at the center of that shift. You'll carry a solution that resonates, lead a company that invests in its salespeople, and operate in a territory with real whitespace. This is a role for someone who wants to build something, not maintain it.
Work Location: This role is fully remote for candidates who reside outside the 30 mile radius of one of our offices. For candidates who reside within a 30 mile radius of one of our offices, this role is Hybrid and would require 3 days a week (T, W, TH) in office.
As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.
Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.
Our total reward package also includes:
- Health, dental, and vision coverage, beginning on the first day of employment. Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 401k saving plan with employer matching.
- Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
- Generous employee stock purchase plan.
- Paid Time Off, Company paid holidays, paid volunteer hours and 12 weeks paid parental leave.
All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.
Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better we are. Five9 is an equal opportunity employer.
View our privacy policy, including our privacy notice to California residents here: https://www.five9.com/pt-pt/legal.
Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.
Similar Jobs
.png)
What you need to know about the Boston Tech Scene
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
