Senior Director, Sales Strategy – Enablement

InvoiceCloud, Inc.

. Support the Chief Revenue Officer (CRO) and broader revenue organization .

Posted 10/5/2026full-timeBoston • Massachusetts • United StatesSenior💰 $240,000 - $250,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in sales strategy, enablement, and operations within enterprise B2B SaaS, with a strong ability to influence cross-functional teams and drive strategic initiatives. Proficient in building dashboards and utilizing AI tools for forecasting and performance measurement.

Highest-signal resume keywords

Sales EnablementSales StrategyGTM PlanningCross-Functional CollaborationAI Tool Utilization

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales MethodologyPerformance MeasurementData AnalysisDashboard CreationQuota ManagementContent CurationCRM IntegrationOKR ManagementPipeline ManagementTerritory Design

Soft Skills

Influencing Without AuthorityStrategic ThinkingEffective CommunicationAdaptabilityTeam Leadership

Tools & Technologies

LMSCMSCRMAI ToolsSales Analytics Software

Industry Keywords

B2B SaaSRevenue OperationsGTM StrategySales OperationsBusiness Operations

Tech Stack

Tools & technologies

Switching

About the role

Key responsibilities & impact

Support the Chief Revenue Officer (CRO) and broader revenue organization
Own sales strategy and enablement priorities and chief-of-staff work for the revenue organization
Connect GTM planning, enablement, operating cadence, sales methodology, technology, content, and performance measurement
Run the CRO's operating rhythm, including agendas, board and QBR materials, OKR cadence, and decision follow-through
Support annual and quarterly GTM planning, including segmentation, territory and coverage design, capacity and quota inputs, and maintaining the sales plan
Run the enablement lifecycle from pre-boarding through onboarding, certification, and continuous coaching
Build dashboards connecting ramp, adoption, certification, pipeline coverage, AI adoption and ROI to win rate, attainment, and forecast accuracy
Embed sales methodology into CRM stages, deal reviews, inspection, and seller workflows
Own and advocate for the LMS/CMS knowledge backbone, including content grooming and curation
Govern sales content and technology by rationalizing the asset library, establishing ownership and intake rules, and driving tool adoption
Own cross-functional strategic initiatives, managing dependencies, accountability, and readouts through completion
Direct GTM AI experimentation, defining pilot requirements and success criteria and determining what should scale or be retired
Set requirements and guardrails for approved AI tools and use AI-assisted forecasting and deal inspection
Translate complex sales, pipeline, enablement, and operating information into board materials, QBRs, decision readouts, and executive communications
Influence Marketing, Product Marketing, Revenue Operations, Customer Success, Finance, and other GTM partners
Connect field observations, enablement performance, pipeline signals, and business outcomes into recommendations for the CRO and revenue leadership team

Requirements

What you’ll need

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

Benefits

Comp & perks

Medical, dental, vision, life & disability insurance
401(k) plan with company match
Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays
Mental health resources
Paid parental leave & backup care
Tuition reimbursement
Employee Resource Groups (ERGs)