Founding Sales Lead

Location: United States; Toronto, Canada About Our Client Our client builds and scales vertical market software companies. They partner with strong teams, invest in the long term, and run disciplined operating systems to drive sustainable growth across their portfolio. About the Product Our client is on a mission to transform the way customers operate. Their AI-powered agent is designed to connect to existing tools, resolve questions, book appointments, and close deals automatically, 24/7, through voice, text, and email. They are a fast-scaling, tech-driven startup backed by leading software investors. The Opportunity We’re hiring a Sales Lead to drive new business growth for our client. This is a full-cycle sales role for an experienced seller who can personally close business, build a repeatable outbound motion, and help shape the go-to-market strategy for a high-growth AI product. You’ll own the sales process from prospecting through close and customer handoff. You’ll be one of the first commercial hires, which means you’ll have real influence on positioning, pricing, sales process, and how the product is brought to market. You’ll work closely with executive leadership and cross-functional stakeholders across Product, Partnerships, Marketing, and Customer Success. This role is designed for someone who thrives in builder environments, is energized by a product that sells itself once prospects see it, and wants ownership over outcomes, not just activity. Requirements Drive New Business Growth Own the full sales cycle: prospecting, discovery, demos, proposals, negotiation, and close. Build and maintain a target account strategy by segment and customer profile. Clearly articulate the ROI, efficiency gains, and revenue impact of AI-powered call handling and booking automation. Seamlessly transition new customers to onboarding and Customer Success for activation and first value realization. Build a Repeatable Outbound Motion Lead outbound strategy and execution across calls, email, LinkedIn, and industry events. Develop and iterate on talk tracks, competitive positioning, objection handling, and demo structure. Establish pipeline creation targets and inspection routines that translate activity into predictable results. Create repeatable playbooks covering segments, sequences, cadences, and qualification criteria. Shape the Go-to-Market Strategy Share structured customer insights and market feedback with Product and leadership to inform roadmap, pricing, and packaging decisions. Maintain accurate pipeline, activity tracking, and forecasting in CRM (HubSpot). Consistently meet or exceed monthly and quarterly KPIs across outreach, demos, pipeline, and revenue. Coordinate with Partnerships and Marketing to leverage partner channels and campaigns for pipeline generation. What Success Looks Like In the First 90 Days You’ve built a clear target account list by segment and launched outbound motions that are producing qualified opportunities. CRM pipeline and activity tracking are clean, reliable, and maintained. You’ve delivered multiple demos, progressed deals through the pipeline, and closed your first customers. In 6 to 12 Months A predictable sales engine is running: outbound activity is converting to qualified pipeline, and pipeline is converting to closed revenue. You’ve closed a meaningful book of new business and the customer base is growing steadily. Sales playbooks, talk tracks, and demo flows are documented and repeatable. You’re contributing to expansion beyond the initial vertical, identifying and testing new market segments. Benefits Required 3 to 5+ years of proven success in B2B SaaS new business sales, with a strong track record of closing. Strong hunter mentality: comfortable with outbound prospecting and generating your own pipeline, not reliant on inbound leads. Experience managing a full sales cycle from first contact through contract execution. Confident running discovery calls and solution-based sales conversations that connect product capabilities to business outcomes. Experience building or materially improving a sales motion: process, messaging, cadence, and forecasting. Strong communication, presentation, and relationship-building skills. CRM experience (HubSpot, Salesforce, or equivalent). Self-motivated, goal-driven, and comfortable working autonomously in a fast-paced, evolving environment. Preferred Experience selling in marine management, storage systems, dealership platforms, or adjacent verticals is a strong plus. Experience selling AI, automation, or voice/conversational technology products. Experience in vertical market software or operationally complex environments where the buyer is an operator, not a tech team. Startup or early-stage SaaS experience where you had to build the motion, not just run it. Why Join Sell a product that prospects can see and hear in action from the first demo, in a market that is ready for it. Ground-floor opportunity: be one of the first commercial hires as the business establishes its leadership team and revenue engine. Direct influence on positioning, pricing, go-to-market strategy, and product direction. Competitive base salary with uncapped commission and high OTE potential.