Senior Director, Sales Strategy & Enablement

InvoiceCloud•Boston, MA

17h

About The Position

InvoiceCloud is a fast-growing fintech leader recognized with 20 major awards in 2025, including USA TODAY and Boston Globe Top Workplaces, multiple SaaS Awards wins for Best Solution for Finance and FinTech, and national customer service honors from Stevie and the Business Intelligence Group. Judges also highlighted our mission to reduce digital exclusion and restore simplicity and dignity to how people pay for essential services, as well as our leadership in AI maturity and responsible innovation. It’s an award-winning, purpose-driven environment where top talent thrives. To learn more, visit InvoiceCloud.com. We are seeking a highly skilled and results-oriented Director/Sr Director Sales Strategy & Enablement to support the Chief Revenue Officer (CRO) and broader revenue organization. This role gives the CRO a single owner for two closely connected priorities: the sales strategy and enablement function, and the chief-of-staff work that keeps the revenue organization running. The role closes the gap between decisions made at the leadership table and execution in the field by connecting GTM planning, enablement, operating cadence, sales methodology, technology, content, and performance measurement. The Director/Sr Director Sales Strategy & Enablement serves as a senior go-to-market operator who can build the analysis, operate credibly at the leadership table, and carry initiatives from decision through field adoption. The role works through influence across Marketing, Product Marketing, Revenue Operations, Customer Success, and Finance and operates effectively amid ambiguity, competing priorities, constant context-switching, and confidential, board-facing work.

Requirements

Approximately 8–12 years of experience across sales enablement, sales strategy or operations, revenue-side chief-of-staff, or Business Operations work within enterprise B2B SaaS.
Experience leading teams.
Demonstrated ability to independently build and interpret the analysis required to support GTM and revenue decisions.
Demonstrated ability to operate credibly with senior leadership and carry strategic initiatives from decision through field adoption.
Proven ability to influence and execute across Marketing, Product Marketing, Revenue Operations, Customer Success, Finance, and other cross-functional stakeholders without relying solely on direct authority.
Ability to operate effectively amid ambiguity, competing priorities, frequent context-switching, and confidential, board-facing work.

Responsibilities

Run the CRO's operating rhythm, including agendas, board and QBR materials, the OKR cadence, and follow-through on decisions, ensuring leadership priorities translate into measurable execution.
Support the annual and quarterly GTM planning cycle in partnership with Finance and Revenue Operations, including segmentation, territory and coverage design, capacity and quota inputs, and maintenance of a single, current sales plan the field can execute against.
Run the enablement lifecycle end to end—from pre-boarding through role-based onboarding, certification, and continuous coaching—with ramp time serving as the primary measure of effectiveness.
Build the dashboard connecting leading indicators—including ramp, adoption, certification, pipeline coverage, and AI adoption and ROI—to leadership outcomes including win rate, attainment, and forecast accuracy.
Embed the sales methodology into CRM stages, deal reviews, inspection, and seller workflows so that a common qualification and value-selling language becomes part of how the field operates rather than a one-time training event.
Own and advocate for the LMS/CMS as the knowledge backbone for AI-driven selling, including content grooming and curation that keeps seller and AI-accessible knowledge accurate, relevant, and current while technical administration remains appropriately owned elsewhere.
Govern content and the sales technology stack with the enablement team by rationalizing the asset library, establishing ownership and intake rules, and driving meaningful adoption of the tools and resources the field is expected to use.
Own the CRO's cross-functional strategic initiatives that fall between teams, actively managing dependencies, accountability, and readouts through completion.
Provide single-point accountability across sales strategy, enablement, and executive operations so that GTM plans inform enablement priorities, operating rhythms reinforce execution, and business reviews identify the next performance gaps to address.
Direct GTM AI experimentation by defining pilot requirements and success criteria, partnering with GTM Engineering on execution, and determining what should scale or be retired based on measurable impact to rep efficiency, win rates, and pipeline output.
Set appropriate requirements and guardrails for approved AI tools—including customer and deal-data access, data handling, and required human review—and use AI-assisted forecast and deal inspection to improve rep efficiency, effectiveness, and output while maintaining accountable human judgment.
Translate complex sales, pipeline, enablement, and operating information into clear agendas, board materials, QBRs, decision readouts, and executive communications that enable timely action.
Influence across Marketing, Product Marketing, Revenue Operations, Customer Success, Finance, and other GTM partners without relying on direct authority, creating alignment around priorities, dependencies, decisions, and execution.
Maintain effective communication and sound judgment in confidential, board-facing, high-ambiguity situations while ensuring decisions and commitments are understood and followed through.
Connect field observations, enablement performance, pipeline signals, and business outcomes into clear recommendations for the CRO and revenue leadership team.