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GtM Planning and Strategy Director



Chicago, IL, USA
Posted on Friday, September 15, 2023

Inclusively is partnering with a leading insurance software company to hire a GtM Planning and Strategy Director. **Please note: this role is NOT an internal position with Inclusively but with the partner company.**


Inclusively is a digital tech platform that connects candidates with disabilities including mental health conditions (e.g. anxiety, depression, PTSD), chronic illnesses (e.g. diabetes, Long COVID), neurodivergence (e.g. autism, ADHD) and other disabilities under the ADA. Applicants with one or more of these conditions are encouraged to apply; Inclusively does not require applicants to disclose their specific disability.

We are currently searching for a GtM Planning & Strategy Director for our Revenue Operations leadership team. A highly cross-functional position, this individual will have purview across the end-to-end customer lifecycle for all our products, businesses, and geographies, driving the most important cross-functional initiatives alongside the SVP Revenue Operations to ensure we meet/exceed overall go-to-market (GtM) business objectives. This leader will regularly interact with executive leaders and their teams (CRO, CCO, CMO, CFO) as well as operational/functional partners to this end, requiring strong communication, analytical, and program management capabilities in a matrixed environment to be successful. This leader will need to be particularly strong in their understanding of managing sales teams and leveraging data/analytics to drive business value (e.g., Pricing).

What You’ll Do

  • Conduct analytics to identify opportunities to improve sales performance, drive price realization, reduce churn, and/or create process efficiencies.
  • Collaborate closely with executive and senior leadership to identify and operationalize revenue opportunities to translate into execution.
  • Manage and maintain the portfolio of strategic programs to improve sales/marketing efficiency, improve implementation practices, and/or retain existing customers by improving the customer experience.
  • Ensure the GtM team continues to make shrewd business and operational decisions as we grow/increase complexity, including maintaining the right short, mid, and long-term orientation.
  • Through indirect management, drive and enable the performance of a high performing team through effective collaboration, clear goal setting in collaboration with direct management, mentorship, roadblock removal, and regular performance feedback in support of our Performance Enablement program.
  • Stakeholder relationship building and coordination to maintain focus and progress against key leadership priorities.
  • Successful program conclusion in the form of tangible sales, retention, or profitability improvements
  • Positive feedback from peers and functional leadership
  • Superior project management and organizational skills with effective, demonstrated approaches to drive cross-functional collaboration and results.
  • Excellent verbal and written communicator with the ability to develop deep trust-based relationships and guide different stakeholder groups directly and indirectly while leveraging persuasive communication skills.
  • Ability to problem-solve real-time and bring an ‘activist’ mentality to change management in an emotionally aware way.
  • Structured thinker with the ability to take initially ill-defined or abstract opportunities / solution ideas and create a structured way of communicating and executing against them.
  • Ability to prioritize time and problem solve to focus on most impactful activities / initiatives.
  • Emotional intelligence to drive to outcomes while maintaining relationships and trust.
  • Superior PowerPoint and Excel capabilities
  • Salesforce experience preferred.
  • Tableau and/or Alteryx familiarity a plus
  • Travel up to 25%

What You’ll Need to Succeed

We’re looking for someone who:

  • Can work hybrid from our Downtown Chicago office

Your experience should include some or all the following:

  • Experience managing projects, preferably in a consulting or sales/marketing/customer operations/transformation context.
  • 3+ years of experience leading substantial commercial programs, consulting projects, and/or operational improvement-focused teams with diverse stakeholders
  • Experience in software/SaaS preferred but not required.
  • 4-year College degree from an accredited university in Business Administration, Economics, Technology, Engineering or related major preferred or equivalent experience
  • MBA preferred.
  • We proudly support and encourage people with military experience, as well as military spouses, to apply.

What You’ll Gain

Benefits from Day One

  • Health insurance plans, dental, and vision
  • Wellness incentives
  • 401(k) and/or RRSP retirement savings plans with employer match

Work-Life Balance

  • Competitive paid vacation time and a free day for your birthday
  • Personal/sick time
  • Paid holidays
  • Flex Time
  • Paid parental leave (U.S. candidates)
  • Volunteer time off