Senior Director, Sales Strategy & Enablement (B2B SaaS)

Location: Greater Boston, United States (hybrid)

Base compensation: $240,000–$250,000 USD annually, plus potential annual bonus or commission.

Company

hirify.global is a fast-growing fintech and SaaS company that provides digital payment solutions for essential services, with a focus on reducing digital exclusion and responsible AI innovation.

What you will do

• Run the CRO’s operating rhythm, including agendas, board and QBR materials, OKR cadence, decision follow-through, and executive communications.
• Lead annual and quarterly GTM planning with Finance and Revenue Operations, covering segmentation, territory and coverage design, capacity, quota inputs, and the sales plan.
• Own the end-to-end enablement lifecycle from pre-boarding and role-based onboarding through certification and continuous coaching.
• Build performance dashboards connecting ramp, certification, pipeline coverage, AI adoption, win rate, attainment, and forecast accuracy.
• Embed sales methodology into CRM stages, deal reviews, inspection, and seller workflows while governing the sales technology and content stack.
• Direct cross-functional GTM initiatives and AI experimentation, defining pilot success criteria, guardrails, and scale-or-retire decisions.

Requirements

• Approximately 8–12 years of experience in sales enablement, sales strategy or operations, revenue-side chief-of-staff, or business operations roles within enterprise B2B SaaS.
• Experience leading teams and independently building and interpreting analysis for GTM and revenue decisions.
• Ability to operate credibly with senior leadership and carry strategic initiatives from decision through field adoption.
• Ability to influence Marketing, Product Marketing, Revenue Operations, Customer Success, Finance, and other cross-functional stakeholders without relying solely on direct authority.
• Ability to work effectively amid ambiguity, competing priorities, frequent context-switching, and confidential board-facing responsibilities.
• Ability to work in a hybrid role based in Greater Boston.

Culture & Benefits

• Medical, dental, vision, life, and disability insurance.
• 401(k) plan with company match.
• Flexible Time Off, wellbeing days, paid holidays, and summer Fridays.
• Mental health resources, paid parental leave, and backup care.
• Tuition reimbursement and Employee Resource Groups.
• Equal employment opportunity and accommodation support during recruitment.