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Key Responsibilities and Required Skills for Chief of Sales

💰 $ - $

SalesExecutiveLeadership

🎯 Role Definition

The Chief of Sales (Head of Sales) is the senior executive responsible for defining and executing the company's revenue strategy, building and scaling a high-performing sales organization, owning quota and forecasting, optimizing go‑to‑market (GTM) motions, and partnering across Product, Marketing, Customer Success and Finance to maximize ARR, gross margin, customer retention, and lifetime value. This role requires a balance of strategic vision, operational rigor, data-driven decision making, and people leadership to deliver predictable, scalable revenue growth.

📈 Career Progression

Typical Career Path

Entry Point From:

  • VP of Sales (Enterprise or Mid-Market)
  • Head of Revenue / Head of Growth
  • Regional Sales Director with P&L accountability

Advancement To:

  • Chief Revenue Officer (CRO)
  • President, Business Unit Lead
  • CEO (for founder/operating-executive trajectories)

Lateral Moves:

  • Head of Global Partnerships
  • GM / Managing Director of a business unit
  • Chief Customer Officer (CCO)

Core Responsibilities

Primary Functions

  • Design, own and execute a multi-year revenue strategy and go‑to‑market (GTM) plan that aligns with company objectives, target markets, product roadmap and investor expectations; translate strategy into quarterly and annual sales plans with measurable KPIs.
  • Set aggressive but attainable ARR/MRR targets and quota frameworks across segments (Enterprise, Mid‑Market, SMB, Channel) and ensure alignment of territory design, product packaging, pricing, and discounting to maximize net revenue and margin.
  • Build, scale and lead a high-performing sales organization by recruiting senior sales leaders, designing compensation plans, defining career paths, implementing coaching programs, and fostering a performance-driven culture focused on customer outcomes and quota attainment.
  • Drive end-to-end sales operations, including pipeline hygiene, CRM governance, opportunity stages, forecasting cadence, commission administration, and sales productivity analytics to improve conversion rates, average deal size, win rates and sales cycle velocity.
  • Lead enterprise selling motions for strategic accounts, personally manage top-tier deals as appropriate, and mentor account executives on complex negotiation tactics, executive sponsorship strategies, and multi-stakeholder deal orchestration.
  • Own revenue forecasting and reporting: develop a reliable, repeatable forecasting process, present monthly/quarterly forecasts to the executive team and board, and take accountability for variance analysis and corrective action plans.
  • Develop and operationalize partnerships and channel strategies (resellers, system integrators, OEMs, strategic alliances) to accelerate growth and expand market reach while protecting direct sales productivity and margin.
  • Partner closely with Marketing to define demand generation priorities, lead qualification criteria (MQL > SQL), content and ABM programs, ensuring marketing and sales alignment on ideal customer profile (ICP), win themes and GTM campaigns.
  • Collaborate with Product to influence roadmap decisions based on market feedback, win/loss analysis, competitive intelligence and customer insights; champion product-market fit and pricing positioning for new offers.
  • Implement a structured sales enablement program—onboarding, playbooks, demo standards, objection handling, and competitive battlecards—so new hires ramp quickly and existing reps continuously improve.
  • Create and continuously refine a customer segmentation and account prioritization model that focuses resources on the highest-potential accounts while balancing acquisition and expansion opportunities.
  • Establish rigorous metrics and dashboards (pipeline coverage, churn, net retention, ACV, LTV:CAC, sales efficiency) and use data-driven insights to optimize capacity planning and go-to-market investments.
  • Manage pricing strategy, discount controls, contract terms and commercialization practices in partnership with Legal and Finance to protect margin and limit commercial risk.
  • Lead cross-functional GTM launches for new products, regions or verticals—define launch plans, enable frontline sellers, coordinate marketing campaigns, and measure launch ROI.
  • Drive a culture of customer-centric selling that emphasizes value-based conversations, outcomes-based ROI selling and success metrics that improve win rates and reduce churn.
  • Establish and refine incentive compensation frameworks and territory alignments that motivate desired behaviors, prevent internal conflict, and align against company revenue and margin goals.
  • Oversee major strategic account plans, renewal and expansion strategies for top-tier customers, and coordinate executive sponsorship to preserve and grow enterprise relationships.
  • Implement competitive intelligence programs including deal post-mortems, win/loss analysis and competitor playbook development to continuously sharpen sales positioning.
  • Lead hiring, succession planning and leadership development for all levels of the sales organization with a focus on diversity, equity and inclusion and on developing future senior leaders.
  • Manage budgets, headcount planning, and sales-related P&L inputs in partnership with Finance; prioritize investments in people, systems and tools to maximize return on sales spend.
  • Champion continuous process improvement: streamline sales workflows, adopt automation and enablement technologies (CRM, CPQ, sales engagement), and reduce administrative overhead to increase seller time selling.
  • Negotiate and close complex commercial agreements for strategic customers and partners, including multi-year contracts, enterprise licensing terms and global rollouts.
  • Represent the company externally at industry events, with key customers and with investors; serve as a credible spokesperson for the company’s commercial strategy and execution.

Secondary Functions

  • Support ad-hoc data requests and exploratory commercial data analysis in partnership with Sales Operations and BI teams to answer business-critical questions and inform strategy adjustments.
  • Contribute to the organization's revenue technology strategy and roadmap, evaluating CRM, CPQ, analytics and enablement tools to scale repeatable sales processes.
  • Collaborate with finance, legal and product teams to translate commercial needs into contract templates, pricing policies and risk controls.
  • Participate in board and investor meetings to present sales performance, market trends, pipeline health and execution plans.
  • Work with Customer Success to ensure coordinated handoffs, define expansion playbooks and minimize churn through proactive account management.
  • Lead cross-functional post-sales reviews and root-cause analysis for retention, onboarding friction or product adoption issues to improve customer outcomes and lifetime value.

Required Skills & Competencies

Hard Skills (Technical)

  • Strategic Sales Planning & GTM Strategy: documented experience designing go‑to‑market plans across segments and channels.
  • CRM & Sales Technology: deep operational experience with Salesforce (or equivalent), CPQ, sales engagement platforms, analytics/BI tools and automation to govern pipeline and forecasting.
  • Sales Analytics & Forecasting: ability to build and interpret dashboards (pipeline coverage, win rates, churn, ARR/MRR metrics) and make data-driven decisions.
  • Enterprise Sales & Complex Negotiation: proven track record negotiating large contracts, multi-stakeholder procurements, and managing procurement/legal/compliance cycles.
  • Channel & Partner Management: designing and scaling reseller, partner and alliance programs, with partner enablement and co-sell motions.
  • Pricing Strategy & Commercial Structuring: experience defining pricing, discounting, packaging and contract terms to protect margin and accelerate deal velocity.
  • Sales Operations & Process Optimization: implementing territory design, quota setting, incentive compensation and operational playbooks that scale.
  • SaaS / Subscription Business Models: metrics-driven understanding of ARR, net retention, CAC payback, LTV and other subscription economics.
  • Financial Acumen: budgeting, sales forecasting, quota modeling and measuring ROI of GTM investments; comfortable presenting to CFO/board.
  • Market & Competitive Intelligence: ability to synthesize vertical trends, competitor positioning and buyer behavior into actionable sales plays.
  • Enablement & Training Systems: designing onboarding programs, playbooks, role-based curriculums and continuous learning frameworks.

Soft Skills

  • Executive Leadership: proven ability to inspire, influence and mobilize cross-functional teams and senior stakeholders.
  • Coaching & Talent Development: strong track record of developing high-performing sellers and leaders through feedback, mentorship and structured development plans.
  • Communication & Storytelling: exceptional verbal and written skills to present strategy, forecast and negotiate at board and C-suite levels.
  • Strategic Thinking with Tactical Rigor: able to balance long-term vision with detailed execution plans and measurable milestones.
  • Customer Empathy & Outcomes Focus: obsession with customer success and driving measurable value in sales conversations.
  • Resilience & Change Management: adept at leading through ambiguity, change and market disruption.
  • Collaboration & Cross-Functional Partnership: history of constructive partnerships with Product, Marketing, Finance, Legal and Customer Success.
  • Problem Solving & Analytical Mindset: chops for diagnosing systemic issues, running post-mortems and implementing root-cause fixes.
  • Ethical Judgment & Integrity: high standards for compliance, contract governance and fair commercial practices.
  • Influence without Authority: ability to secure buy-in from stakeholders across the company, including remote and regional teams.

Education & Experience

Educational Background

Minimum Education:

  • Bachelor's degree in Business, Marketing, Finance, Engineering or related field (or equivalent professional experience).

Preferred Education:

  • MBA or advanced degree in Business, Strategy, or relevant discipline; executive education in leadership, negotiation or data-driven sales preferred.

Relevant Fields of Study:

  • Business Administration
  • Marketing
  • Finance
  • Computer Science / Engineering (for product-led & enterprise tech sellers)
  • Economics

Experience Requirements

Typical Experience Range:

  • 10+ years in progressive sales leadership roles with at least 5 years leading a large sales organization or multiple sales functions (direct sales, channels, operations) and proven quota-bearing executive performance.

Preferred:

  • Prior experience as VP/Head of Sales, GM or CRO in mid-market or enterprise software, SaaS, cloud, technology, or complex B2B services.
  • Demonstrated success scaling revenue from seed/Series A through scale-up phases and preparing organizations for IPO or M&A.
  • Experience building and managing global or multi-region sales teams, with cultural sensitivity and remote team operations experience.
  • Track record of achieving double-digit ARR growth, improving net retention, and optimizing sales efficiency (e.g., improving sales cycle and increasing average deal size).
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