CaptivateIQ, Inc.

Account Executive - Enterprise

CaptivateIQ, Inc.$300K *
US-AnywhereRemote in Toronto, ON
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years of SaaS sales experience, focusing on net-new Enterprise deals for 4-5 years
  • Demonstrated success in exceeding quotas and closing multi-stakeholder deals over $250K
  • Expertise in leading independent product demos with strong technical articulation
  • Familiarity with sales methodologies like MEDDPPICC or Challenger
  • Self-starter mentality with a commitment to accountability and improvement
  • Strong communication and stakeholder management abilities

Responsibilities

  • Own the complete Enterprise sales cycle from sourcing to closing deals
  • Create strategic account plans that address customer pain points
  • Conduct engaging product demos that connect solutions to stakeholder needs
  • Develop an in-depth understanding of the CaptivateIQ platform
  • Collaborate with cross-functional teams to enhance pipeline and deal progression
  • Maintain disciplined sales practices with accurate forecasting
  • Adapt sales strategies based on customer feedback and market trends
  • Help shape sales playbook and go-to-market strategies during growth phase

Benefits

  • 100% coverage for medical, dental, and vision insurance, with 75% for dependents
  • Flexible vacation days and quarterly mental health days
  • One-time anniversary expense contribution for personal use
  • Annual stipends for professional development and caretaking
  • 401k plan for future savings
  • Provision of the latest Apple products for optimal work performance
  • Supportive Employee Resource Groups (ERGs) enhancing DEI initiatives
Full Job Description
About the Role

As an Enterprise Account Executive at CaptivateIQ, you'll drive net new enterprise acquisition across complex, multi stakeholder deals in high value accounts. You'll own the full sales cycle from self sourced pipeline generation through discovery, demo, and close while helping build and scale the next phase of our Enterprise team.

This is an opportunity to join CaptivateIQ at a pivotal stage of our growth as we continue to invest in and expand our Enterprise business. We're looking for strategic, product fluent sellers who thrive in ambiguity, take initiative, and connect technical product depth to real customer outcomes. This is a high ownership role for someone who brings curiosity, grit, coachability, and the ability to lead value based conversations across multiple stakeholders, including CFOs, CROs, and VP level leaders, and who is excited to help shape the future of our Enterprise sales motion.

Responsibilities

  • Own the full Enterprise sales cycle - from self-sourcing pipeline through discovery, demo, and close
  • Develop and execute strategic account plans aligned to customer pain and business outcomes
  • Lead compelling, self-run product demos that tie solution capabilities to stakeholder needs
  • Build and maintain deep knowledge of the CaptivateIQ platform and how it solves complex challenges
  • Collaborate cross-functionally with solutions engineering, product, marketing, CS, and BDRs to drive pipeline and deal momentum
  • Maintain a disciplined pipeline with accurate forecasting and clear deal progression
  • Continuously evolve your sales approach using customer feedback, competitive insights, and market trends
  • Contribute to the development of our sales playbook and GTM strategy as we scale


Requirements:

  • 8+ years of SaaS sales experience, including 4-5 years owning net-new Enterprise deals
  • Proven track record of exceeding quota and closing complex, multi-stakeholder deals in the $250K+ range
  • Experience leading product demos independently, with strong technical and value articulation skills
  • Proficiency in sales methodologies such as MEDDPPICC, Challenger, or similar
  • Self-starter with a strong bias for action, accountability, and continuous improvement
  • Excellent communication, discovery, and stakeholder management skills


Nice to Have

  • Deep understanding of how to sell into operational and finance buyers (e.g., CFO, RevOps, Finance leaders)
  • Familiarity with compensation, planning, analytics, or adjacent SaaS categories
  • Familiarity with sales tools like Salesforce, Gong, and Outreach


Benefits

  • (US-ONLY) 100% of medical, dental, and vision covered including 75% for dependents
  • Flexible vacation days and quarterly mental health days so you can recharge
  • Enjoy a one-time expense on your 1-year work anniversary (to use for travel, home furnishings, fancy meal)
  • Annual stipends for professional development and caretaking
  • (US-ONLY) 401k plan to participate in and save towards the future
  • Newest Apple products to help you do your best work
  • Employee Resource Groups (ERGs) to support and celebrate the shared identities and life experiences of communities within CaptivateIQ. ERGs directly support our company-wide DEI goals as a space for developing and retaining diverse talent



$300,000 - $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 $300,000 OTE. 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.

About CaptivateIQ, Inc.

CaptivateIQ is a software company that provides a platform for managing sales commissions. The company's platform enables sales teams to calculate and manage their commissions in real-time, reducing errors and increasing transparency. CaptivateIQ's clients include some of the world's leading sales organizations, such as Salesforce, HubSpot, and Zoom. The company was founded in 2017 and is headquartered in San Francisco, California.
Learn more about CaptivateIQ, Inc.
Size
50 employees
Industry
Net Income
-$2 million
Founded
2017
5 Year Trend
+10%
Revenue
$10 million

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