Director, Sales Strategy – Planning

This is a fully remote position, open to applicants in United States.

📋 Description

• Conduct weekly reviews of forecasts and pipelines across North America and EMEA.

• Establish agendas, prepare analytical insights, challenge existing assumptions, document decisions, and ensure action items are executed.

• Maintain an independent, data-driven forecast in conjunction with representative submissions, clarifying any discrepancies between the two perspectives.

• Oversee pipeline coverage for the current quarter as well as the next two quarters.

• Develop path-to-plan scenarios and assess the implications of key deals being delayed.

• Lead the analytical preparation and follow-up for quarterly business reviews and discussions with sales leadership.

• Equip the Chief Sales Officer (CSO) for executive and board meetings with performance narratives, metrics, risks, inquiries, and suggested actions.

• Cultivate trusted relationships with sales representatives throughout North America and EMEA.

• Evaluate opportunity quality, closing strategies, next steps, deal aging, and forecast categories with representatives.

• Mentor on deal management, pipeline oversight, and forecasting techniques.

• Collaborate with channel sales and Business Development Representative (BDR) leadership to review the pipeline and pinpoint gaps in coverage, handoff, conversion, and follow-up.

• Work in partnership across Sales, Channels, BDR, Marketing, Product, Finance, and Customer Success to tackle cross-functional pipeline and deal challenges.

• Team up with Revenue Enablement to identify skill deficiencies and create targeted programs, certifications, practice sessions, call reviews, and coaching initiatives.

• Participate in call reviews and offer constructive feedback on discovery, qualification, deal strategy, and subsequent steps.

• Assess the impact of enablement programs on seller behavior, deal quality, conversion rates, ramp-up, and other key outcomes.

• Collaborate with the CSO and Finance on annual and quarterly sales planning, capacity, hiring and ramp assumptions, coverage, territories, quotas, and pipeline needs.

• Analyze pipeline generation, conversion rates, win ratios, sales cycles, renewals, partner contributions, and productivity segmented by region, segment, product, and seller group.

• Lead win/loss and competitive analysis in conjunction with Product and Marketing teams.

• Review quota and compensation frameworks, discounting strategies, pricing exceptions, and deal desk trends.

• Develop scenarios and recommendations in collaboration with Finance and the CSO.

• Translate approved decisions into actionable requirements for Sales Operations, RevOps, Finance, Marketing, and Revenue Enablement.

• Validate business data utilizing Salesforce reports, sales data, call intelligence, and planning models.

• Identify misleading metrics or workflows across various stages, forecast categories, territories, quotas, compensation structures, and sales processes.

• Create practical AI applications for account preparation, call reviews, coaching, deal assessments, forecasting, and sales strategy.

• Test AI methodologies and integrate successful practices into the sales routine.

• Collaborate with the Sales & GTM Operations Manager on data definitions, dashboards, CRM enhancements, and seller workflows.

⛳️ Requirements

• A minimum of seven years of experience in Sales Strategy, Sales Planning, Sales Operations, Revenue Operations, or a similar analytical role within the B2B technology sector.

• Extensive hands-on experience in Sales Operations, covering forecast management, pipeline scrutiny, Salesforce reporting, territory or quota planning, and sales process design.

• Proven experience supporting enterprise sales teams across various regions, along with experience working with direct sales, BDR, and partner or channel strategies.

• Background in coaching sellers or sales leaders through deal reviews, call evaluations, pipeline assessments, or structured enablement initiatives.

• Strong modeling capabilities and the ability to construct an independent forecast, capacity plan, and scenario analysis.

• Familiarity with SQL or business intelligence tools is advantageous.

• Practical knowledge of AI tools and the discernment to apply them to sales tasks in ways that enhance quality and efficiency.

• Capability to distill complex analyses into clear recommendations for executive audiences.

• Credibility to challenge senior leadership, engage directly with representatives, and gain trust without formal authority.

• Proficient in using Salesforce, call intelligence tools, BI and reporting tools, Excel/Google Sheets, Claude, and other AI and GTM instruments.

• Flexibility to work standard business hours while accommodating North America and EMEA time zones.

• Willingness to travel occasionally, up to 15% of the time.

• Ability to fulfill stated physical requirements, including prolonged sitting, close vision, effective hearing, communication, and manual dexterity.

🏝️ Benefits

• Occasional travel (up to 15%) for sales kick-offs, quarterly business reviews, and interactions with sales teams in North America and EMEA.

• Standard working hours with the flexibility to accommodate forecast cycles, quarter-end activities, board preparations, and teams across North America and EMEA time zones.

• Reasonable accommodations provided throughout the application, interview, and employment processes.

• Commitment to equal opportunity employment.

• At-will employment status.