Director of Strategy & Analytics

Location: Chicago, IL (or remote)

Compensation: $150–200K (incl. bonus) + equity

Experience: 3–6+ years at top‑tier consulting firm (MBB) or similar

Reports to: Chief Financial Officer

About Perennial Services Group (PSG)

Perennial Services Group is a rapidly growing platform of over 30 local brands spanning landscaping, turf, pest control, arbor, irrigation, and plant health care services. We support our brands with centralized marketing, sales, and operations infrastructure to drive scalable, sustainable growth in competitive local markets.

Role Overview

We are looking for a Head of Strategy & Analytics to help drive performance across our portfolio of home services brands.

This role sits at the intersection of data, strategy, and execution. You will own how we measure performance, generate insights that matter, and work directly with Presidents, GMs, and leadership to improve outcomes across the business.

This is a hands‑on role. You will be expected to build dashboards, work directly with data, and translate analysis into clear actions that drive measurable results across PSG. It is the perfect off‑ramp for top‑tier consultants wanting to move from advising on strategy to owning outcomes, combining hands‑on data work with operational impact across a scaled, multi‑brand platform.

Key Responsibilities

• Performance Visibility: Build and maintain dashboards across all brands, connecting data from operating systems into a unified data layer (ideally Snowflake) to provide clear visibility into key operating and financial metrics.
• Insight Generation & Execution: Analyze performance across brands, regions, and channels to identify what is driving results; translate insights into clear actions and work closely with Presidents, GMs, and the CRO to implement and track improvements.
• Strategic Initiative Support: Partner with leadership on cross‑brand strategic initiatives (e.g., procurement savings, cross‑sell playbooks, pricing optimization); use data to size opportunities, guide execution, and scale successful approaches across PSG.
• Turnarounds & Performance Improvement: Support underperforming brands by identifying root causes across marketing, sales, and operations; develop focused action plans across both revenue growth and cost‑saving initiatives, and drive implementation.
• AI Strategy & Implementation: Identify, test, and scale AI solutions across sales, service, operations, and analytics; define success metrics, measure impact, and ensure initiatives drive real business value.

Required Skills & Experience

• Analytical rigor + business judgment: Proven ability to move from data to insight to action; strong problem‑solving skills with a focus on what actually drives performance.
• Hands‑on data capability: Strong SQL skills and/or experience with BI tools (Power BI, Tableau, Looker, etc.); comfortable working with data warehouses (e.g., Snowflake) and connecting data across systems.
• Operator mindset: Experience working closely with business leaders; able to translate analysis into practical, implementable changes alongside Presidents and GMs.
• Background: 3–6 years of experience in strategy, analytics, or similar roles; experience at a top‑tier consulting firm (e.g., MBB) or in a high‑performing analytics, BizOps, or RevOps environment strongly preferred.
• Communication & influence: Clear, concise communicator who can simplify complex analysis and build credibility with both operators and leadership teams.

What This Role Is Not

• Not a strategy role disconnected from execution
• Not a passive reporting or dashboarding function
• Not a data engineering role

This is a hands‑on role focused on driving measurable improvement across the business.

What Success Looks Like in Year 1

• Establish a trusted set of dashboards used across PSG to manage performance
• Improve data quality and consistency across brands and systems, enabling more reliable decision‑making
• Identify and execute high‑impact strategic initiatives that drive measurable results
• Support turnarounds in underperforming brands, leading to clear KPI improvements
• Successfully pilot and scale 1–2 AI initiatives that deliver tangible business impact
• Become a trusted partner to Presidents, GMs, and leadership, balancing analytical depth with practical execution

Why Join Perennial?

At Perennial, you’ll make a visible impact across dozens of brands while building a function from the ground up. This role offers the opportunity to shape how decisions are made across the organization and to drive meaningful, measurable improvement at scale.

If you want to work at the intersection of data, strategy, and real‑world execution, we’d love to meet you.

Compliance & Employment Requirements

Equal Opportunity Employer

Perennial Services Group is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, national origin, sex, sexual orientation, gender identity or expression, age, disability, veteran status, or any other protected characteristic under applicable law.

E‑Verify Participation

Perennial Services Group participates in the U.S. Department of Homeland Security’s E‑Verify program to confirm the employment eligibility of all newly hired employees. Candidates must be legally authorized to work in the United States.

Physical Requirements

This position is primarily remote and involves computer‑based work performed from a home office environment. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions. Typical requirements include:

• Prolonged periods of sitting, typing, and working at a computer
• Reliable internet access and an appropriate workspace for virtual collaboration
• Ability to participate in video calls and virtual meetings
• Occasional travel to PSG offices, brand locations, or team events as needed (generally infrequent)