Wayleadr is hiring a Director of Sales to drive Annual Recurring Revenue growth. You’ll be responsible for delivering strong ARR growth for EOY 2026 and 2027, focusing primarily on new logo acquisition in the corporate office vertical, with a secondary focus on expanding existing customers. You will personally carry a quota while guiding the broader Sales team on process excellence.

What You'll Do

Grow ARR by +$2.2M, to $9.0M, by EOY 2026.
Deliver +$2.2M from new logos and expansions outside our ‘top 5’ logos.
Focus on growth selling into the Corporate Office vertical while maintaining the baseline in the Multifamily Housing vertical.
Build a repeatable outbound motion for Enterprise.
Vet the efficacy of email, LinkedIn, and other direct channels for a low-volume, high-customization approach.
Work with Customer Success to align on a sustainable model to process customer referrals.
Strengthen internal Sales processes, ensuring strong qualification activities (e.g., MEDDPIC) especially around ICP adherence.
Define role clarity with Sales, between Customer Success and Support.
Align consistently with Product regarding feasibility of customer build requests.
Establish rigorous Sales metrics reporting to inform leadership (pipeline tracking by channel, sales cycle times, $ ARR attributable by rep).
Own the deal forecasting process.

What We're Looking For

Proven track record of delivering significant quota and ARR growth in a B2B SaaS environment.
Experience building and executing a repeatable outbound sales motion, particularly to enterprise clients.
Deep understanding of sales methodologies and qualification frameworks like MEDDPIC.
Strong analytical skills to define and report on key sales metrics.
Ability to personally carry a quota while coaching and guiding a sales team.
Collaborative approach to working cross-functionally with Product, Customer Success, and Support.