Senior Director, Strategy & Execution

Ensono; Downers Grove (IL); Remote; USD 205,000 - 278,000; Full time

Benefits offered by this job

Unlimited Paid Days Off

Health plan options

401k with company match

Dental, vision, disability, life and A

Family Forming Benefit

Paid parental leave

Education reimbursement

Sabbatical leave

Wellness program

Flexible work schedule

Job summary

Ensono is seeking a senior strategy leader to shape and execute the company’s strategy. You will translate strategy into action, lead critical initiatives, and influence executive decisions near the CEO, President, ELT and investors.

This role focuses on strategic leadership, governance, and broad business understanding, with a path to broader executive strategy leadership and ownership over time.

Qualifications

• 10+ years in corporate strategy, strategy operations, consulting or chief-of-staff roles.
• Proven enterprise planning with portfolio governance and executive readouts.
• Original strategic thinking that changed direction or offerings.
• Strong financial fluency: P&L and EBITDA impact.

Responsibilities

• Lead strategy development and execution with regular exposure to the CEO and ELT.
• Own the annual strategy process end to end, including gates and memos.
• Drive corporate development, M&A diligence, and partnerships.
• Shape operating-model changes and build an AI-enabled strategy office.
• Coordinate executive forums, client advisory programs and board material.

Skills

Strategic thinking

Executive communication

Problem solving

Program governance

AI productivity tools

Data-driven decisions

Education

Bachelor's degree

Job description

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.

About the role and what you'll be doing:

Ensono’s Strategy team sets the company’s annual strategy, turns it into a governed portfolio of strategic initiatives, focuses corporate development, and runs the executive forums that keep the CEO, the executive leadership team (ELT) and the board focused on what matters most.

This role sits at the center of how Ensono sets and executes strategy, with regular exposure to the CEO, President, executive team, board and investors. It is designed as a path to broader strategy leadership, with growing ownership of the strategy cycle, corporate development and executive forums over time.

We are looking for a senior strategy leader who can both help shape the strategy and drive execution. You will own the machinery that translates strategy into action, lead critical initiatives personally, influence executive decisions, and develop a broad understanding of every aspect of Ensono's business.

This is not a project management or governance role. Program discipline is table stakes; the job requires judgment, business acumen and original thinking. You will spot the initiative that is drifting before it misses, write the memo that frames the decision and, from a vista point close to every part of the business and its leaders, genuinely shape Ensono’s strategy with ideas of your own.

This role is ideal for a highly strategic, intellectually curious leader who wants to influence the direction of a growing company while building the experience required for future executive-level strategy leadership positions.

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.

About the role and what you'll be doing:

Ensono’s Strategy team sets the company’s annual strategy, turns it into a governed portfolio of strategic initiatives, focuses corporate development, and runs the executive forums that keep the CEO, the executive leadership team (ELT) and the board focused on what matters most.

This role sits at the center of how Ensono sets and executes strategy, with regular exposure to the CEO, President, executive team, board and investors. It is designed as a path to broader strategy leadership, with growing ownership of the strategy cycle, corporate development and executive forums over time.

We are looking for a senior strategy leader who can both help shape the strategy and drive execution. You will own the machinery that translates strategy into action, lead critical initiatives personally, influence executive decisions, and develop a broad understanding of every aspect of Ensono's business.

This is not a project management or governance role. Program discipline is table stakes; the job requires judgment, business acumen and original thinking. You will spot the initiative that is drifting before it misses, write the memo that frames the decision and, from a vista point close to every part of the business and its leaders, genuinely shape Ensono’s strategy with ideas of your own.

This role is ideal for a highly strategic, intellectually curious leader who wants to influence the direction of a growing company while building the experience required for future executive-level strategy leadership positions.

Shape the strategy from close to the business

• Sit in on executive leaders’ staff meetings to stay close to the business and to give as well as take, keeping leaders current on company priorities and what is moving elsewhere in Ensono.
• Connect the dots across functions, spot emerging risks and opportunities early, and bring them to the CSO, CEO and President with a clear point of view.
• Contribute original ideas to the strategy, from new offerings and market moves to operating-model changes, and turn the strongest into strategy memos and initiative proposals.
• Help the CEO and President do their jobs better by anticipating what they need and turning what is happening across the business into content for the ELT and the board.

Run the annual strategy cycle and initiative portfolio

• Own the annual strategy process end to end, from theme intake and charters to strategy memos, decision gates and the executive strategy session, improving it each cycle.
• Stand up each approved initiative with a charter, sponsor, accountable lead, plan and measures of success, and hold the portfolio to account through the ELT, senior leadership team, monthly business review and board rhythm.
• Surface risks, dependencies and decisions early, and elevate with a clear recommendation rather than a status update.
• Coach initiative leads on problem structuring, root-cause analysis and decision-ready writing, and maintain the templates and toolkit that make good submissions easy.
• Personally lead one or two of the high-priority initiatives or special projects each year.

Drive the executive operating rhythm

• Coordinate and run the monthly business review: shape the agenda with the CEO and President, work with each leader on their content, hold the quality bar on what is presented, and follow through on the decisions and actions that come out of it.
• Run the other forums the Strategy team owns, including the weekly AI program standup, initiative readouts and critical-issue tracking for the CEO.
• Prepare and pressure-test materials for the ELT, the board and its committees, and our private equity sponsor, including directly helping produce the CEO’s board content.
• Track decisions and actions to closure, and turn meetings into crisp summaries that people act on.

Lead corporate development and strategic analysis

• Help identify where acquisitions, joint ventures or partnerships are the right path and, when one is chosen, source and screen options and support diligence and integration.
• Evaluate and shape joint ventures and partnerships, including client-anchored models: frame the rationale for every party, build the business case and prepare partner discussions.
• Scope and manage external advisers and specialists, from statement of work through final readouts.
• Lead market and competitive intelligence, including competitor results, market studies and the impact of AI on our markets, and translate it into implications for leadership.

Steward executive client and market programs

• Co-lead the Executive Advisory Council, Ensono’s forum of client executives: member recruitment and onboarding, agenda design, meeting delivery, and synthesis of what members tell us.
• Connect advisory council and voice-of-the-client insight to the strategy process and to initiative priorities.

Shape transformation and build the strategy office

• Help shape operating-model changes, such as governance and intake for a proposed enterprise PMO, and own other transformation programs as assigned.
• Build an AI-enabled strategy office: dashboards, agents and automated summaries that reduce manual coordination and give leaders answers without having to ask.
• Represent the Strategy team across the executive and senior leadership teams, and deputize for the SVP and CSO in forums as needed.

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.

Required Qualifications:

• 10 or more years in corporate strategy, strategy operations, consulting, corporate development or a chief-of-staff role, including 3 or more working directly with C-suite executives.
• A track record of running an enterprise planning or strategic initiative process across multiple functions, including portfolio governance, decision gates and executive readouts.
• Evidence of original strategic thinking: ideas you originated that changed a company’s direction, offerings or operating model.
• Strong structured problem solving and financial fluency: business cases, P&L and EBITDA impact, contract economics and investment theses.
• Executive-grade communication, from a six-page narrative memo to a one-slide board summary.
• The ability to lead without authority and hold senior leaders accountable, often people more senior than you.
• The presence to sit in senior leaders’ staff meetings as both listener and contributor, and the judgment to know what to share and what stays in the room.
• Rigorous program management habits (charters, plans, risk logs, status reporting) used as a means rather than the end.
• Hands‑on fluency with AI productivity tools, data and dashboards.
• Absolute discretion with confidential information, including transactions, board matters and personnel.
• A bachelor’s degree.
• 10% travel requirement, primarily for executive strategy sessions, advisory council meetings, client engagements and acquisition diligence

Preferred Qualifications:

• An MBA or equivalent graduate degree.
• Experience in IT or managed services, mainframe or hybrid cloud, or enterprise B2B technology.
• Hands‑on M&A, joint venture or partnership experience, including diligence and integration.
• Experience in a private equity-backed company, including board and investor reporting.
• Experience running a customer advisory board or executive client program.

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 $205,000 to $278,000 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 [e-mail].