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Home Flexible Job Board Head of GTM, Sales Planning

$270,000–300,000/yr 24d ago

Head of GTM, Sales Planning

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CaptivateIQ

Toronto

Full-time Permanent Remote

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Summary

The role involves owning the full go-to-market lifecycle for Sales Planning, including market positioning, sales motion development, and customer expansion. You will partner with cross-functional leadership to align strategy, influence product roadmaps, and drive revenue performance.

Job Description

CaptivateIQ is transforming the way companies plan, manage, and optimize sales performance. We started by revolutionizing incentive compensation management, and now we're expanding our platform to solve broader sales planning challenges. Recognized by industry analysts like Forrester and G2 and backed by top-tier investors, including Sequoia, ICONIQ, Accel, and Sapphire Ventures,  we empower high-growth companies like Netflix, Figma, and Stripe with the flexibility and insights needed to drive revenue performance.

Join a talented, fast-growing team committed to solving some of the most complex and impactful problems in sales performance management.

About the Role

This role owns the numbers half of marketing, including demand, ops, field, and BDR, while a separate Head of Corporate Marketing owns brand, product marketing, and narrative. We're deliberately splitting what used to be one CMO seat into two focused leadership roles, each hired for depth rather than breadth. 

This is a full-ownership role — you’ll define how these products are sold, implemented, and grown, and you’ll work directly with enterprise customers from the earliest stages of evaluation through long-term success. You’ll report to the Co-CEO and partner closely with Product, Engineering, CX, and GTM.

This role is balanced equally between pre-sales and post-sales. You’re not just winning deals — you’re owning the full customer lifecycle from close through expansion.


\n

Responsibilities

  • Own the full GTM lifecycle for Sales Planning — from market positioning through customer go-live and expansion. Catalyst will also fall under this role as a smaller, secondary objective
  • Define go-to-market strategy, including positioning, packaging, and the use cases that deliver the most value for revenue and finance leaders
  • Develop and operationalize the sales and implementation motion, and bring Product, CX, and GTM along on the strategy
  • Evaluate the effectiveness of our current Sales Planning GTM motion and be open to evolving the approach — including testing dedicated or overlay selling models — based on market feedback and customer outcomes
  • Partner with EPD leadership to influence product decisions that impact GTM success — use case prioritization, positioning, and implementation requirements — while respecting that EPD owns final decisions on product development and platform architecture
  • Work closely with Product to translate market feedback into a roadmap that builds toward durable, scalable revenue
  • Drive product-market fit validation across the highest-signal use cases by engaging directly with customers and analyzing customer data
  • Form and test hypotheses on how to accelerate awareness, conversion, and adoption across the full funnel from lead to renewal
  • Serve as the escalation point for customer issues — not to manage every escalation directly, but to identify thematic patterns and drive systematic process fixes
  • Partner with cross-functional leaders across Product, Engineering, CX, and GTM to align on strategy, build the enablement needed to sell and support both products at scale, and hold the organization accountable to execution
  • Surface customer and market insights to leadership to inform product direction, company strategy, and where we invest next
  • Today, Sales Planning GTM resources are allocated across implementation, CX, and GTM functions — you’ll coordinate their work through dotted-line relationships. As the product scales, you’ll build a dedicated team reporting to you

Requirements

  • 10+ years of experience in sales performance management, revenue operations, or enterprise SaaS
  • Deep expertise in Sales Planning — territory design, quota methodology, capacity modeling. Ideally, you’ve worked at a Sales Planning vendor (Anaplan, Varicent, Xactly) or services firm implementing SPM, or you’ve led a Sales Planning rollout in-house at an enterprise company. A combination of domain expertise and go-live experience is ideal
  • Demonstrated experience building or scaling an enterprise SaaS product’s go-to-market and implementation motion
  • Strong presence with enterprise buyers — comfortable owning the commercial and technical conversation with senior revenue and finance leaders
  • Proven ability to drive alignment across Product, Engineering, CX, and GTM teams without relying on positional authority
  • Comfortable operating in a product that is still finding its footing in enterprise — able to make scope calls, set expectations, and move forward without perfect information
  • Familiarity with incentive compensation management and how it connects to sales planning is a strong plus
  • Experience with partner-led or SI-driven implementation motions is a plus
  • Exposure to AI-powered product capabilities or agentic workflows is a plus

Benefits

  • Comprehensive Healthcare: 100% coverage for medical, dental, and vision for all FTEs, with roughly 75% coverage for dependents.
  • Flexible Time Off: Flexible vacation days plus quarterly mental health days to ensure you have the space to recharge.
  • Annual Stipends: Dedicated funds for your professional development and caretaking needs.
  • Work Anniversary Bonuses: Annual bonuses to celebrate your milestones and contributions to the CaptivateIQ team that grow as your tenure does.
  • Retirement Savings (US-Only): A 401(k) plan to help you invest in and secure your future.
  • Premium Tools: The latest Apple hardware to empower you to do your best work.
  • Inclusive Community: Active Employee Resource Groups (ERGs) that celebrate shared identities and support our DEI goals by fostering an environment where diverse talent thrives.

Notice for Prospective Candidates

  • Only emails from @captivateiq.com should be trusted.

We are aware of active recruitment scams using the CaptivateIQ name, in which individuals pose as our recruiters and post fake remote job openings and make fake job offers on the Internet. Please note, we will never do the following:

  • Attempt to correspond with a candidate using a free web-based account, such as an email address that ends in @gmail.com, @yahoo.com, @hotmail.com, etc.
  • Make an offer of employment without conducting multiple rounds of interviews face-to-face using secure video-conferencing technology.
  • Ask candidates to cash checks to buy equipment on behalf of CaptivateIQ.
  • Ask candidates to make a payment in order to be considered for a position.
  • Make early requests for candidates' personal information such as date of birth, passport details, credit card numbers, bank details and social security number, etc.
  • Please note that we’ll only ask for more sensitive personal information in connection with background checks after an offer is made.

\n$270,000 - $300,000 a yearThe compensation offered for this position will depend on numerous factors, including individual proficiency, anticipated performance, and the location of the selected candidate. The OTE salary range for this role is $270,000-$300,000. Compensation for candidates hired in Canada will be provided in Canadian dollars and may differ from the ranges listed above due to currency conversion. Our OTE is just one component of CaptivateIQ's competitive total rewards package, which also includes equity, comprehensive health benefits, and other perks and benefits.\n

CaptivateIQ participates in E-Verify, web-based system that allows enrolled employers to confirm the eligibility of their employees to work in the United States

About the company

CaptivateIQ

CaptivateIQ is rebuilding compensation and sales planning for the age of AI. CaptivateIQ was named a Leader in the 2026 Gartner® Magic Quadrant™ for Sales Performance Management, a Leader in The Forrester Wave™ for SPM Solutions for Incentive Compensation, and the #1 sales compensation software on G2 — recognition built on the same platform that brings quota, territory, headcount, and compensation into a single, AI-powered workspace for agility, alignment, and scale.

The platform's AI agents are built directly into SmartGrid, CaptivateIQ's real-time modeling architecture, designing, running, and adapting the systems behind go-to-market execution with the speed and precision today's revenue leaders demand. Purpose-built for modern revenue teams, CaptivateIQ bridges the gap between incentive compensation management and sales planning, so strategy, execution, and measurement operate in perfect harmony.

Legacy solutions and spreadsheets weren't designed for dynamic go-to-market organizations. CaptivateIQ replaces slow, error-prone, siloed processes with a unified platform that seamlessly connects sales planning, incentive management, and performance tracking — giving revenue leaders one shared source of truth from capacity planning to payout.

CaptivateIQ empowers every function — RevOps, Finance, Sales, and more — to adjust plans, incentivize performance, and deliver on revenue growth targets, all within a flexible environment that adapts as quickly as business does.

Trusted by industry-leading organizations including Affirm, Boston Scientific, and Netflix, CaptivateIQ is the intelligent sales performance management (SPM) platform setting the new standard for revenue teams. Learn more at www.captivateiq.com.

Your plans, your way: plan for anything, pivot anytime.

Founded

2017

Company size

201-500 employees

Industry

Software Development

Org type

Privately Held

Headquarters

San Francisco, California

Apply Now

About the company

CaptivateIQ

CaptivateIQ is rebuilding compensation and sales planning for the age of AI. CaptivateIQ was named a Leader in the 2026 Gartner® Magic Quadrant™ for Sales Performance Management, a Leader in The Forrester Wave™ for SPM Solutions for Incentive Compensation, and the #1 sales compensation software on G2 — recognition built on the same platform that brings quota, territory, headcount, and compensation into a single, AI-powered workspace for agility, alignment, and scale.

The platform's AI agents are built directly into SmartGrid, CaptivateIQ's real-time modeling architecture, designing, running, and adapting the systems behind go-to-market execution with the speed and precision today's revenue leaders demand. Purpose-built for modern revenue teams, CaptivateIQ bridges the gap between incentive compensation management and sales planning, so strategy, execution, and measurement operate in perfect harmony.

Legacy solutions and spreadsheets weren't designed for dynamic go-to-market organizations. CaptivateIQ replaces slow, error-prone, siloed processes with a unified platform that seamlessly connects sales planning, incentive management, and performance tracking — giving revenue leaders one shared source of truth from capacity planning to payout.

CaptivateIQ empowers every function — RevOps, Finance, Sales, and more — to adjust plans, incentivize performance, and deliver on revenue growth targets, all within a flexible environment that adapts as quickly as business does.

Trusted by industry-leading organizations including Affirm, Boston Scientific, and Netflix, CaptivateIQ is the intelligent sales performance management (SPM) platform setting the new standard for revenue teams. Learn more at www.captivateiq.com.

Your plans, your way: plan for anything, pivot anytime.

Founded

2017

Company size

201-500 employees

Industry

Software Development

Org type

Privately Held

Headquarters

San Francisco, California

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