About this role.
Five9 is seeking an Enterprise Sales Director to win new cloud contact-center software customers across a Northeast territory. The role owns the full sales cycle, including prospecting, pipeline generation, C-level engagement, forecasting, business planning, and closing enterprise and transactional opportunities. Candidates need substantial enterprise software sales experience, with preference for contact-center software expertise and familiarity with the assigned territory. This fully remote US role is quota-driven and requires a disciplined, independent hunter who can work effectively in a fast-changing team environment.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would segment the territory by ideal customer profile, current contact-center maturity, and trigger events such as platform migrations or customer-experience initiatives. I would combine targeted account plans, executive outreach, partner referrals, industry events, and disciplined cold calling, then measure conversion at each funnel stage to reallocate effort quickly.
I would explain the customer challenge, stakeholder map, competitive landscape, and business case I developed. I would emphasize how I created mutual action plans, aligned executive sponsors, addressed risk and procurement concerns, and maintained accurate forecasts until the deal closed.
I focus on strategic outcomes rather than product features, such as customer experience, operational efficiency, agent productivity, business continuity, and revenue retention. I tailor the business case to each executive's priorities and use quantified discovery findings to connect the solution to measurable impact.
I maintain clear stage definitions, next steps, close plans, stakeholder information, and risk notes for every material opportunity. I forecast from evidence such as validated pain, decision process, budget, executive sponsorship, and mutual commitments, rather than relying on optimism or close-date assumptions.
I block recurring time for prospecting while protecting dedicated account-planning and deal-strategy sessions for priority opportunities. I use segmentation, automation, and measurable activity targets to sustain top-of-funnel coverage, while advancing high-value opportunities through focused stakeholder engagement and mutual action plans.
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.
The Enterprise Sales Director creates, identifies, and closes sales within North and Central America or a set of named accounts. The Sales Director’s primary responsibility is to acquire new customers and drive revenue. A successful Sales Director is a self-starting closer who can create a large pipeline of business within a short period of time. We hire professionals who have a minimum of 10 years operating, selling, or servicing customer contact/engagement centers for Sales or Service. Your relevant experience is paramount to being considered. Candidates should possess a high level of professionalism, persistence, focus, and ability to execute while selling or serving our customers.
We look for business athletes who are aggressive team players – hungry, nimble and intelligent – with the ability and willingness to close a mix of complex enterprise and more transactional deals.
States include: Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, New York, New Jersey, Pennsylvania and Connecticut.
Key Responsibilities:
- Create and drive revenue within a specified region or list of named accounts
- Generate business opportunities through professional networking and cold-calling
- Drive brand awareness, campaigns, and lead generation via networking, associations, etc.
- Meet and exceed all quarterly and annual sales quotas
- Own the sales cycle from lead generation to closure
- Develop business plan and present the business plan during quarterly review sessions
- Maintain account and opportunity forecasting within our internal forecasting system (SFDC)
- Self-generate leads from a personal connections, referral partners, and regional networking events
- Ensure 100% customer satisfaction and retention throughout the Implementation and Support experience
Key Qualifications:
- 5+ years of outside enterprise software sales experience
- Be able to work independently and as part of a team in a fast pace, rapid change environment
- Experience selling at the C-level
- Proven track record of sales excellence
- A proven sales hunter and closer
- Superior professional presence and business acumen
Preferred Qualifications:
- Contact Center Software Sales in less than 1,000-seat space
- Knowledge of territory or accounts assigned
Work Location: This role is fully remote.
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.
The US base salary range for this role is below.
$106,800—$264,700 USD
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.
This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.




