• Identify and qualify semi-complex sales opportunities by calling on small to mid-sized prospects and clients • Focus primarily on high volume and transactional sales opportunities • Participate in strategic selling conversations and client demos in partnership with applicable sales leader(s) as requested • Generate opportunities and leads through prospecting, networking, and marketing • Demonstrate the value propositions of WellSky’s offerings and services and communicates that to different types of clients • Track, maintain, and report sales pipeline, opportunities, and contact information in Salesforce • Participate in reoccurring forecasting meetings with sales management • Achieve quarterly goals related to lead generation, pipeline management, and quota attainment set by WellSky • Perform other job duties as assigned

• Own the full enterprise sales cycle from prospecting to close • Identify, prioritize, and develop strategic relationships with top software organizations • Develop deep product knowledge and demonstrate strong technical fluency in the AI prototyping space • Partner closely with founders and engineers to feed customer insights into product direction • Shape and refine GTM motion, especially around expansion, pricing, negotiation, and existing inbound playbooks

• Lead the creation and execution of comprehensive enterprise account growth strategies, including QBRs and senior stakeholder engagement. • Drive incremental revenue and EBA token consumption through up sell and cross sell motions into new, adjacent, and upgraded products. • Own and lead negotiation and closure of complex Enterprise Business Agreement (EBA) expansion deals, often tied to renewal based quota structures. • Execute strategies to expand buyer seats across business units, personas, and buying groups within assigned enterprise accounts. • Oversee pipeline and forecasting accuracy for seat expansion and upsell/cross sell opportunities across enterprise accounts.

• You'll own the full sales cycle: prospecting and qualifying enterprise accounts, running discovery with VP+ engineering and product leaders, navigating complex buying processes, and closing six- to seven-figure contracts. • You'll work directly with our founder to shape positioning, refine our ICP, and build the playbook for the sales organization we're growing. As the early sales leader here, you will have clear paths into management roles as we scale the team.