Enterprise Sales Director - Midwest/Mid-Atlantic

Company: Five9
Location: Cleveland
Posted on: February 18, 2026

Job Description:

Job Description Job Description 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 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. Based in Ohio preferred. 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. 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 Experience selling to COO/CFO Knowledge of territory or accounts assigned Work Location: This role is fully remote for candidates who reside outside the 50 mile radius of our San Ramon office. For candidates who reside within 50 miles of our San Ramon location, this role is Hybrid and would require 3 days a week (M, W, TH) in our San Ramon 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. 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.

Keywords: Five9, Detroit , Enterprise Sales Director - Midwest/Mid-Atlantic, Sales , Cleveland, Michigan