Opportunity

Five9 Sales Director: Enterprise SaaS Career Growth in Columbus

Location Columbus
Company Five9
Source jobicy
Posted 2026-08-25 14:58:22

Career & Market Insight

Compensation & Market Positioning: The base salary range of $106,800–$264,700 USD is wide, reflecting the seniority ladder for an enterprise sales director. OTE (on-target earnings) with commission, performance bonuses, and ESPP will likely push total comp well above $300K at the high end — competitive with enterprise SaaS sales director benchmarks in the Northeast US market.

Skills & Career Development: This role builds high-value, transferable skills:

  • Complex enterprise SaaS sales cycles — highly sought after in cloud/CCaaS markets
  • C-suite executive engagement and negotiation
  • Salesforce (SFDC) pipeline management and forecasting
  • Cloud contact center domain expertise — a growing segment with strong demand

Company Signals: Five9 is a publicly traded, established cloud contact center provider (NASDAQ: FIVN), not a scrappy startup. This signals relative job stability, structured processes, and a defined sales methodology — suitable for experienced closers who don't want to build from scratch.

Green Flags: 100% employer-paid health premiums, 12 weeks parental leave, and mental health support are standout benefits. The 10+ years minimum experience requirement signals they are serious about hiring proven talent, not developing junior reps.

Red Flags to Watch: The very wide salary band suggests compensation is highly variable and likely heavily commission-dependent. Candidates should push for clarity on quota attainment rates, average ramp time, and territory maturity before accepting an offer.

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 every day 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.

Territory States: 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 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
  • Ability to work independently and as part of a team in a fast-paced, rapidly changing 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 experience in less than 1,000-seat space
  • Knowledge of assigned territory or accounts

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 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 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 savings 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.

US Base Salary Range: $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.

Frequently Asked Questions

Is this Enterprise Sales Director role truly fully remote?
The posting states the role is fully remote; however, it covers a defined territory across Northeastern US states including New York, New Jersey, Massachusetts, and Pennsylvania. Candidates should expect regional in-person client meetings and networking events within this geography.
What is the salary range for this role at Five9?
The US base salary range is $106,800–$264,700 USD. Total compensation may also include an annual performance bonus, stock options, an employee stock purchase plan, and other incentive compensation.
How much experience is required to apply for this position?
Five9 requires a minimum of 10 years operating, selling, or servicing customer contact or engagement centers, plus at least 5 years of outside enterprise software sales experience with a proven track record of C-level selling.
What benefits does Five9 offer for this role?
Five9 covers 100% of the employee portion of health, dental, and vision insurance from day one, offers a 401(k) with employer matching, 12 weeks paid parental leave, paid volunteer hours, a generous ESPP, and access to a mental health support platform.
Is experience with contact center software required?
It is listed as a preferred qualification — specifically, experience with Contact Center Software Sales in the sub-1,000-seat space and knowledge of the assigned territory or accounts. It is not listed as a hard requirement but would strengthen a candidate's application.
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