Head of GTM, Sales Planning

GTMnow; Toronto; Hybrid; CAD 270,000 - 300,000; Full time

Benefits offered by this job

Healthcare: 100% coverage

Flexible time off

Professional development stipends

Work anniversary bonuses

Apple hardware

DEI ERGs

Job summary

CaptivateIQ is hiring for a senior leader who will own the numbers half of marketing, spanning demand, ops, field, and BDR. You’ll shape how products are sold, implemented, and grown, partnering with enterprise customers from evaluation to long-term success.

You’ll report to the Co-CEO and collaborate with Product, Engineering, CX, and GTM. This role is split between pre-sales and post-sales, owning the full customer lifecycle from close through expansion.

Qualifications

• 10+ years in sales performance or revenue operations.
• Deep expertise in Sales Planning (territory design, quota modeling).
• Experience launching enterprise SaaS GTM & implementation.
• Strong enterprise buyer experience with senior leaders.
• Ability to align Product, Engineering, CX, GTM.
• Familiar with incentive compensation and sales planning.
• Experience with partner-led or SI-driven implementations is a plus.
• Exposure to AI-powered capabilities is a plus.

Responsibilities

• Own the full GTM lifecycle for Sales Planning.
• Define go-to-market strategy and use cases.
• Develop and implement sales and implementation motion.
• Evaluate and evolve the current GTM motion.
• Collaborate with EPD to influence product decisions.
• Work with Product to translate market feedback into roadmap.
• Drive product-market fit validation with customers.
• Test hypotheses to accelerate awareness, conversion, adoption.
• Serve as escalation point for customer issues.
• Coordinate cross-functional teams to scale.
• Surface insights to leadership for strategy.

Skills

Sales Planning

GTM strategy

Enterprise SaaS

Executive engagement

Cross-functional

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.

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.

$270,000 - $300,000 a year

The 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.

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