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Director, Go To Market Strategy & Planning

Ensono -
Chicago, IL

Quick Apply

Job Details

Full-time
$155,000 - $210,000 a year

Benefits

Wellness program
AD&D insurance
Disability insurance
Health insurance
Dental insurance
Flexible spending account
Tuition reimbursement
Adoption assistance
Work from home
Parental leave
Vision insurance
401(k) matching
Loan assistance
Flexible schedule

Qualifications

Financial sensitivity analysis
Marketing ROI (MROI) improvement
Google Sheets
Financial model construction
Sales analytics & reporting tools
Customer segmentation analysis
Dynamic financial modeling
Market segmentation analysis
Sales data analysis
Data-driven problem-solving
Presentation creation
Google Slides
Consulting firm experience

Full Job Description

Director, GTM Strategy & Planning

At Ensono, our Purpose is to be a relentless ally, disrupting the status quo and unleashing our clients to Do Great Things! We enable our clients to achieve key business outcomes that reshape how our world runs. As an expert technology adviser and managed service provider with cross-platform certifications, Ensono empowers our clients to keep up with continuous change and embrace innovation.

We can Do Great Things because we have great Associates. The Ensono Core Values unify our diverse talents and are woven into how we do business. These five traits are the key to achieving our purpose: Honesty, Reliability, Curiosity, Collaboration, and Passion.

This is a newly created role! We're looking for a strategic operator who can take ambiguity and turn it into a plan. This role owns the future of our go-to-market motion—how we define our ideal customers, where we deploy sales capacity, how we set targets, and how we measure what's working. You'll be the analytical backbone behind annual planning, territory design, and executive-level strategic analysis.

This is not a Revenue Operations execution role — it's a thinking role, partnering directly with the VP of Revenue Operations and the executive team to shape how Ensono goes to market. Someone who can independently frame the right questions, design the right approach, and recommend the path forward.

Strategic Planning

Lead annual and quarterly GTM planning: market sizing, segment prioritization, and resource allocation
Own territory design and capacity modeling—balancing coverage, fairness, and revenue potential
Drive quota setting and compensation plan design in partnership with Finance and Sales Leadership
Build and maintain account stratification frameworks to focus sales energy on the highest-value opportunities
Define and refresh the Ideal Customer Profile (ICP) — including the scoring criteria, strategic rationale, and where and why we draw the line

Analytics & Insights

Build CAC and ROI analysis frameworks to evaluate GTM investments across headcount, marketing spend, and channel mix
Deliver Board- and ELT-ready strategic analysis — not just data, but a point of view and a clear recommendation
Partner with BI/Analytics to mine Salesforce and other data assets to surface actionable insights

Cross-Functional Partnership

Collaborate with Sales, Finance, Marketing, and Product to align on GTM decisions and drive them forward
Translate business strategy into operational models that Sales Ops can execute
Challenge assumptions, pressure-test forecasts, and flag risks early

Team Development

Lead and develop a small team
Build repeatable frameworks and templates that scale beyond yourself
Be ready to roll up your sleeves — this is a builder role from day one

We want all new Associates to succeed in their roles at Ensono. That's why we've outlined the job requirements below. To be considered for this role, it's important that you meet all Required Qualifications. If you do not meet all of the Preferred Qualifications, we still encourage you to apply.

What You Will Need:

7–10+ years of experience, including 3+ years in management consulting (e.g., McKinsey, Bain, BCG, Deloitte S&O, Accenture Strategy, or equivalent)
Demonstrated builder orientation — you've created GTM frameworks from the ground up: ICP design, territory and capacity modeling, quota and comp planning, or CAC/ROI analysis
Advanced Excel/Google Sheets and PowerPoint/Slides skills — you've built board-level deliverables
Financial modeling skills across capacity plans, ROI models, and scenario analysis
Strong executive presence — you've presented to and held your own at the board and ELT level
Strong data acumen — you can independently identify the right questions, partner with BI/Analytics to pull what you need, and translate the output into insight

Bonus Qualifications

MBA or equivalent graduate degree
Experience in B2B technology, SaaS, managed services, or infrastructure/cloud services
Familiarity with sales planning tools (e.g., Salesforce, Clari, Anaplan, Pigment)

Why Ensono?

Ensono is a place to make better happen – for our clients and for your career. You can do great things through innovation or collaboration, by learning or volunteering, or to promote diversity and inclusion. You can do great things for your own health or for a healthier planet. Whatever it means to you to do great things we want Ensono to be the place you can do it.

We are a client-facing business, but we do encourage clients to allow us to work remotely most of the time so if you are not required to be on a client site, you can choose to work from home or in our Ensono offices.

Some of our benefits include:

Unlimited Paid Days Off
Three health plan options
401k with company match
Eligibility for dental, vision, short and long-term disability, life and AD&D coverage, and flexible spending accounts
Family Forming Benefit including fertility coverage and adoption/surrogacy reimbursement
Paid childbearing and paternal leave
Education Reimbursement, Student Loan Assistance or 529 College Funding
Sabbatical leave
Wellness program
Flexible work schedule

As of the date of this posting, a good faith estimate of the current pay scale for this role is $155,000 to $210,000 annually based on a full-time schedule. Please note that placement in the range may vary based on numerous factors including but not limited to skills, experience, internal equity, and business needs. In addition to base salary, other compensation programs, depending on eligibility, include an annual bonus plan based on company and individual performance and an equity grant under our Associate Equity Appreciation Program.

Ensono is an Equal Opportunity/Affirmative Action employer. We are committed to providing equal employment to our Associates and building a diverse and inclusive workforce. All qualified applicants will be considered without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, or other legally protected basis, in accordance with applicable law.

Pay transparency nondiscrimination statement/posting OFCCP's pay transparency policy can be found on OFCCP's website.

If you need accommodation at any point during the application or interview process, please let your recruiter know or email [email protected].

Quick Apply

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