The role: Drive qualified pipeline for high-value custom development projects ($60K120K+) through strategic outbound to enterprise buyers. Own prospecting, qualification, and SQL handoff to technical teams.
What you'll do:
- Outbound execution Build targeted account lists (Apollo), craft personalized sequences (Smartlead), manage LinkedIn outreach, and track in HubSpot
- Lead qualification Run discovery calls to validate: budget authority, technical requirements (APIs, integrations, multi-location complexity), decision timelines, stakeholder mapping
- Campaign optimization A/B test messaging, analyze reply rates, iterate based on data (not vanity metrics)
- Pipeline ownership Weekly reporting: accounts touched, SQLs generated, conversion rates, deal velocity
- Market intelligence Feed back: buyer objections, competitor intel, pricing benchmarks, messaging effectiveness
Must-haves:
- 46 years B2B tech sales Selling custom development, SaaS platforms, enterprise software, or technical services (not products)
- High-ticket experience Proven track record closing or generating pipeline for $50K+ deals with 36 month cycles
- Technical fluency Can hold conversations with CTOs, Engineering Managers, IT Directors about APIs, integrations, and system architecture
- Outbound craft Your cold emails get replies. You research accounts, personalize at scale, and know the difference between good and bad copy
- CRM discipline Comfortable with Apollo, HubSpot, Smartlead (or equivalents). You track, you learn, you iterate
- Self-starter mentality No hand-holding. You build lists, test hypotheses, and own outcomes
Strong advantages:
- Experience selling to hospitality, retail, or multi-location operators
- Knowledge of loyalty platforms, POS systems, and property management systems
- Agency or custom dev shop background (you understand project scoping, technical discovery, implementation complexity)
- Experience with partnership-led sales (channel partnerships, referral programs, co-marketing)
