Director, Global Sales Enablement

The Role 

The Director of Global Sales Enablement is a strategic business partner responsible for transforming insightsoftware's go-to-market capabilities. You will own the complete product-to-field loop—converting product strategy, product marketing, and competitive intelligence into field-ready playbooks and stage-mapped sales content, then systematically closing the loop back to Marketing with structured feedback on message efficacy and audience fit. 

This is not a training function. This is a revenue accountability function. You will be measured on tangible business outcomes: ramp time, quota attainment, win rates, stage conversion, and field adoption of core methodologies. You will report to sales leadership and Revenue Operations with the data and credibility to influence strategy. 

This is not a traditional program-management enablement role. We need a leader who can combine strategic thinking, team leadership, cross-functional influence, and operational rigor to build the systems, programs, and rhythms that improve field effectiveness at scale. You will lead teams, make decisions with incomplete information, navigate organizational complexity, and drive adoption through influence—not authority. You'll move between strategic planning (annual enablement roadmap), tactical execution (launching a sales play), and coaching (developing managers).  

If you're looking for a specialist role—deep expertise in a single domain like LMS administration or training facilitation—this is not the right fit. 

Key Responsibilities 

Content Ownership & the Product-to-Field Loop 

• Own the full bidirectional content loop: translate product strategy, product marketing output, and competitive positioning into field-ready playbooks, use-case libraries, and stage-mapped sales content. 

• Act as the product fluency translator for the field—ensure reps and managers understand why insightsoftware's solutions matter in the Office of the CFO, not just what they do. 

• Close the loop back to Product Marketing with structured, data-driven feedback on messaging resonance, buyer persona fit, and what landed in the field versus what fell flat. 

• Report on enablement quality through both quantitative signals (win rates, stage velocity, ramp curves) and qualitative field feedback (what messaging stuck, what objections remain, what competitive gaps need closure). 

• Maintain centralized, versioned content repositories with clear ownership, refresh cadences, and retirement standards—ensure the field never relies on outdated collateral. 

• Keep pace with insightsoftware's evolving product portfolio, AI roadmap, and market positioning—content must reflect where the business is today and where it's heading. 

• Build and own a certification and content framework for the channel partner ecosystem, ensuring partners have the product fluency, messaging alignment, and sales readiness to represent insightsoftware effectively in the market. 

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Field Intelligence & Data-Informed Priorities 

• Act as the critical conduit between what the field is experiencing in the market and what performance data reveals about patterns, gaps, and opportunities. 

• Synthesize qualitative intelligence (what reps are hearing in discovery, what objections derail deals, what messaging resonates with CFOs and Controllers) with quantitative signals (ramp velocity, conversion rates, attainment, deal velocity by motion). 

• Bring that synthesis to Product Marketing, Product Leadership, and Sales Leadership in a form that drives decisions—not just informs them. Use data to build the enablement roadmap, prioritize content, and flag competitive or product gaps. 

• Create feedback loops that give Product and Marketing visibility into what's actually working in the field, enabling them to iterate and evolve messaging ahead of market shifts. 

Common Language & Inspection Frameworks 

• Define and own the common language and frameworks used across the global sales organization for pipeline inspection, opportunity qualification, forecast methodology, and deal progression. 

• Ensure core sales methodologies (MEDDPICC, Value Selling, or insightsoftware-customized variants) are embedded into how reps think and how managers inspect—not just how they complete training. 

• Build enablement infrastructure that connects formal sales stage definitions to the field's working vocabulary and buyer journey frameworks, reducing translation friction. 

• Standardize how managers inspect, coach, and develop talent, creating consistency across regions and cohorts. 

Manager Enablement & Coaching Consistency 

• Design and deploy structured manager development programs that build consistency in how front-line leaders inspect pipeline, coach reps, and develop talent. 

• Elevate manager enablement to a first-class strategic investment—not an afterthought delegated to individual discretion. 

• Partner with Sales Leadership to establish shared coaching standards, inspection cadences, and performance accountability across all regions and verticals. 

• Equip managers with the tools, frameworks, and confidence to be multipliers of field productivity. 

• Move fast: enablement programs should be sharp and continuously improving—not perpetually under construction. 

Measurement & Accountability 

• Build a data-driven enablement function with transparent KPIs tied directly to business outcomes: ramp curve (30/60/90-day productivity), quota attainment rates, win rates, stage-specific conversion rates, and forecast accuracy. 

• Establish a culture of accountability for the enablement team and the field, where impact is visible, programs are measured, and continuous improvement is evidence-based. 

• Report monthly to Sales Leadership and Revenue Operations with credible data that enables decisions about team structure, investment, and go-to-market changes. 

• Track the ROI of major enablement initiatives (new methodology rollout, sales plays, certification programs) to justify resource allocation and identify what drives impact. 

Field Leadership Partnership and Delivery  

• Operate as a genuine strategic business partner to Sales Leadership—assertive, direct, and willing to challenge the field constructively when standards are not being met. 

• Embed enablement into key sales moments: QBRs, pipeline reviews, deal strategy sessions, product launch planning, territory assignments, and competitive wins/losses. 

• Hold field leaders accountable to the standards, frameworks, inspection disciplines, and methodologies that enablement establishes. 

• Ensure field leadership owns their teams' adherence to frameworks and actively coach to methodology—enablement builds the programs, but sales leaders enforce adoption. 

Qualifications 

• 8+ years of experience in sales enablement, sales management, or a combination thereof, with at least 3 years managing a function (team, budget, P&L accountability). 

• Proven track record of scaling enablement from early-stage to hyper-growth in a B2B SaaS or Enterprise software company serving executive buyer personas (CFO, VP Finance, Controller, etc.). 

• Business fluency in the Office of the CFO—understand the challenges, priorities, and language of Finance leaders. You don't need to be a CFO, but you need to know what keeps them awake at night and how they evaluate software investments. 

• Deep expertise in modern sales methodologies (MEDDPICC, Value Selling, or equivalent frameworks). You have trained on these, coached to them, built inspection frameworks around them, and measured their impact. 

• Full product-to-field content loop ownership—you've built the bidirectional flow from PMM to field, gathered structured feedback on message quality and audience fit, and fed that back into marketing strategy. 

• Demonstrated ability to synthesize field signals, rep feedback, performance data, and competitive intelligence into clear enablement and go-to-market priorities. 

• Manager-level program experience—you've built and scaled coaching programs for front-line managers, not just rep-level training. You understand how to build systems for consistency at scale. 

• Relentless problem-solver with a bias for action. You move forward without waiting for perfect teams, perfect tools, or budget cycles. You get things done. 

• Strong executive presence and the ability to challenge field leadership constructively in QBRs, strategy sessions, and 1-on-1s. 

Preferred 

• Multi-product or multi-motion sales experience—you've navigated enablement in complex go-to-market environments (land, expand, upsell; different buyer personas; multiple vertical or use-case strategies). 

• Familiarity with financial software, FP&A, consolidation, or compliance solutions for the Office of the CFO. 

• Experience Planning Global SKO’s for large organizations.   

• Experience working with channel or partner ecosystems and scaling enablement across indirect sales organizations. 

• Data literacy and analytics fluency—you're comfortable pulling and interpreting sales data, building KPI dashboards, and using analytics to make decisions. 

• Background in building remote-first or globally distributed teams and enabling asynchronous, self-serve enablement models. 

What To Expect 

First 30 Days: Rapid Audit & Quick Wins 

• Conduct a rapid audit of the current state: content library, onboarding programs, inspection frameworks, CRM playbooks, and field feedback mechanisms. Map what exists, what's working, and what gaps exist. 

• Meet with Sales Leadership, Product Marketing, Product Management, and front-line managers across geographies. Listen to what the field is saying—what's landing, what's not, where they're struggling. 

• Identify the two or three highest-priority initiatives that will move fastest and begin mobilizing immediately, without waiting for full onboarding or additional hiring. 

• Establish baseline KPIs: current ramp curve (by function), quota attainment rates, win rates, stage conversion times, and rep adoption of core frameworks. 

First 60 Days: Foundation & Traction 

• Launch or materially overhaul onboarding by function, prioritizing BDRs and Account Executives. Define success metrics (time to first deal, time to quota contribution, ramp velocity). 

• Establish the product-to-field content loop with clear ownership, refresh cadence, feedback mechanisms, and decision rights. Ensure PMM understands what messaging is landing and what isn't. 

• Define the enablement KPI framework and establish baseline measurements. Set targets for ramp improvement, methodology adoption, and field feedback quality. 

• Conduct initial sales methodology audit—understand where MEDDPICC, Command of the Message, or other frameworks are currently deployed and where they're not. Begin designing remediation. 

• Build enablement roadmap (6-12 month view) and socialize with Sales and Product Marketing. Set quarterly milestones tied to business priorities. 

One-Year Outlook: Measurable Impact 

• Ramp Curve: Demonstrably faster time-to-productivity for new hires, with cohort data showing improvement (e.g., 30-day pipeline contribution up X%, 60-day quota contribution up X%). 

• Content System: Evergreen, versioned content repository that keeps pace with product and strategy changes—actively informs PMM and Product on competitive and messaging gaps. 

• Methodology Adoption: Consistent manager inspection and coaching practices across all regions and functions, with measurable adoption of core frameworks and documented improvements in deal quality and forecast accuracy. 

• Strategic Partnership: Sales Leadership views enablement as a revenue driver and a source of field intelligence. Enable decisions are part of go-to-market strategy, not reactions to ad hoc requests. 

• Field Accountability: Structured feedback from the field on product, messaging, and competitive positioning flows back to Product and Marketing on a regular cadence, informing roadmap and positioning decisions.