Vice President of Sales

Raleigh, NC /
Revenue Organization – Sales /
Full Time
As the Vice President of Sales you will lead the Sales, Sales Development, and Account Management teams. You are responsible for achieving business growth targets through effective management and leadership of a high performance sales organization. In doing so, you will develop and execute on both short- and long-term strategic plans to achieve aggressive sales targets and expand our customer base. You will partner extensively with leadership across the company to acquire, retain, cross-sell, and up-sell customers in support of 15Five’s long-term growth.

A person who will excel in this role is someone experienced in value-based selling to mid-market and enterprise businesses, and exhibits a strong executive presence with sound business judgement. The ideal candidate knows how to use data-informed analysis to champion new initiatives internally, while learning and failing fast. This role requires a strategic leader that is equal parts creative, operational, collaborative, and revenue-minded. The Vice President of Sales will report to the Chief Revenue Officer of 15Five. 


    • Sales Strategy Development and Execution
    • Develop strategy, goals, and quarterly strategic objectives and key results (OKRs) in partnership with the team and cross-functional leaders in support of company growth targets
    • Identify and address areas of improvement throughout the buyers journey to optimize the sales cycle and conversion rates
    • Partner with Marketing and senior leadership to build and continually refine a holistic go-to-market strategy
    • Strategize with Product to align the product roadmap with the demands of the market
    • Collaborate with Customer Success to ensure new customers have a seamless experience and are set up for long-term success

    • Team Leadership in Revenue Generation and Performance
    • Implement and adjust the sales performance metrics and hold the sales team accountable to milestones and objectives to drive high performance and engagement of all team members
    • Coach, mentor, and provide actionable feedback to sales team members to help them achieve their professional and personal growth goals
    • Create and sustain an excellent sales culture within 15Five, recruiting top talent, harnessing competitive spirits toward overachievement, and cultivating a team selling mentality
    • Conduct all of 15Five’s Best-Self Management practices according to schedule: Best-Self Kickoff, Strength’s Discovery, OKR setting, weekly 15Fives, regular 1:1s, Best-Self Reviews, High Fives, etc.
    • Evangelize and model company values, Senior Leadership Team messaging, company policies/ guidelines, tool and process usage, and Best-Self Management practices

    • Customer Centricity and Market Understanding
    • Foster relationships with prospects in order to understand their needs, uncover objections, and ensure their success
    • Approach all prospect and customer interactions with integrity, ensuring discretion and confidentiality when needed
    • Bring an executive presence and influence to customer conversations in support of sales reps
    • Provide a “voice of the customer” and “voice of the market” to our product and go-to-market strategies

    • Metrics: Budgeting, Reporting, and Forecasting
    • Set and manage the yearly sales budget
    • Work with Revenue Operations to provide regular reporting to the Revenue Leadership Team and Senior Leadership Team on achievement of key performance indicators
    • Submit a detailed and dependable sales forecast each week to help inform strategic decisions


    • Prior experience managing high performing sales management teams with a consistent track record of hitting revenue goals.
    • 15 years of overall sales experience (at least 5 leading the team), building relationships with Fortune 1000 companies and managing complex sales processes with multiple stakeholders and negotiations with pricing based on value, legal and procurement.
    • Experience leading a team in a Team Selling environment.
    • Demonstrated a successful track record as an individual contributor and the ability to share relevant and complex closing experience with a growing team.
    • The ability to get into the field and into deals with your team; leveraging your experience as a closer to drive efficiencies in the sales process.
    • The understanding that this is a high growth startup that requires a hands-on and entrepreneurial style.


    • Complete 15Five’s new-hire onboarding and job-specific training for the Revenue Organization / Sales Role
    • Complete the Best-Self Management Certification Course
    • Complete the Best-Self Kickoff with each direct report 
    • Align on Forecast Methodology 
    • Identify needs for your team and role, and build out your OKRs for the quarter
    • Align with Sales Leaders, learning strengths, and diving into Best-Self Management 
    • Learn and understand customer segments, and current marketing strategies 
    • Evaluate current processes for efficiency/accuracy


    • Hiring strategy defined and implemented, in close partnership with Talent Team
    • Every member of the Sales Team is improving through an organized training program and real-time coaching
    • Deliver the Quarterly Business Review to the SLT
    • The Sales Team is unified with high morale and engagement


    • You’ve achieved record breaking revenue results as a team
    • All hiring goals are met with high performing AEs in all regions


    • Monday: Share your wins with the company on our Monday Boost. Celebrate your team and set clear priorities for the week. Join or help lead Sales Training. 
    • Tuesday: 1:1 meeting with your manager. Participate in the cross-functional Sales and Marketing bi-weekly meeting. Hold 1:1s with Team Members. Join or help lead Sales Training.
    • Wednesday: Share current KPIs and Sales Forecast in the Revenue Leadership Team Meeting 
    • Thursday: Lead the Sales Leadership Team Meeting to identify and address pressing issues throughout the Sales organization,
    • Friday: Friday standup is the best part of your week. 50+ people sharing wins for the week and discussing our early ‘call’ for next week. Celebrate all the deals that have closed this week!


    • Open to vulnerability, self-reflection, and candid feedback to grow personally and professionally
    • Curious and committed to innovation, continuous learning, and growth 
    • Self-motivated, self-responsible, and self-accountable
Full-time, salaried exempt position. Typical work week: Monday through Friday, 8 am to 6 pm. Flexible schedule while working an expected 40+ hours/week. Possible early-morning or after-hours requirements due to support across various time zones. 


15Five is a people and performance platform that instantly upgrades each and every manager. It works by combining employee engagement, continuous performance management, and manager effectiveness software with education, services, and community. At the heart of our approach is Best-Self Management, an evidence-inspired strategy for cultivating world-class managers and transforming organizations by unlocking every employee’s potential. With our holistic solution, CEOs, HR leaders, and managers create highly-engaged, high-performing organizations.  

We work with over 2,000 forward-thinking companies that use our solution to bring out the best in their people, including big brand names like Credit Karma, WP Engine, Adobe, and Fitbit. 15Five is backed by Next 47, Origin Ventures, Point Nine Capital, and Matrix Partners. Its headquarters are based in San Francisco, with offices in New York and Raleigh, NC. The company is working 100% remotely during the COVID-19 pandemic. 

We’re excited to continue building out a diverse team that prioritizes inclusivity and celebrates everyone’s unique identity. To support our people, 15Five believes in flexible working arrangements, non-gendered Parental Leave, Flexible Time Off, Sick Time Off and extensive training and development including but not limited to Diversity, Equity & Inclusion, Best-Self Management, strengths discovery and alignment and Manager specific development opportunities. 

Research shows that while men apply for jobs when they meet an average of 60% of the criteria, womxn and other underrepresented folx tend to only apply when they check every box. So, if you think you have what it takes but don't necessarily meet every single point listed below, please apply - you could be exactly who we are looking for! 

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