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Spyglass Ops

Head of Operations - Creatively Innovative

united states / Posted
APPLY

Link to apply listed at the bottom of this Job Description. Only applications submitted through this link will be considered.


WHO WE ARE

Creatively Innovative is a results-driven digital marketing agency specializing in high-volume, seasonal service industries. We help home service businesses — including pressure washing and Christmas light installation companies — generate consistent, qualified leads through paid search and SEO. We've built a proven fulfillment model that delivers real results for real clients, and we're growing fast.


Our mission is to build a self-managing agency that creates lasting impact for our clients and enables our team to do their best work — without the founder needing to be the glue holding it all together.


Our Core Values are:


  • State of the Art Innovation - It's in the name. We are constantly working on new & innovative ways to improve our practices.
  • Efficient - We are well-organized and efficient individuals, always working to optimize our processes.
  • Attention To Detail - We are meticulous, and pay extreme attention to the details.
  • Results Driven - We have a results-driven work ethic through accurate and consistent data tracking.
  • Collaboration - We value working together as a team to bring in ideas all across the board.
  • Hard Working - We are dependable & reliable individuals who work hard in everything we do


**If our mission does not resonate with you, please do not bother applying.



JOB DESCRIPTION

The Creatively Innovative team is looking for a seasoned, systems-minded Head of Operations with a proven track record in digital marketing agencies or high-volume service businesses. This is not a role for someone learning on the job — we need an operator who has built this kind of machine before and knows exactly what to do when handed the keys.


The Head of Operations is responsible for architecting a true single source of truth across our fulfillment systems, building radical ownership into our team culture, and making the day-to-day run without the CEO's involvement in quality control. You'll bring structure to a fast-moving agency environment, turning fragmented tools and manual processes into a scalable, automated fulfillment engine.


The application code word is EMPOWER. The Head of Operations is a highly skilled strategic thinker. They anticipate and solve problems in a self-directed way. They empower and build a team around them to move fast while maintaining culture and quality.


This is a full-time, 1099 remote position. Given the critical nature of this role, we host a rigorous, 4-part application process.


RESPONSIBILITIES

Systems & Operations


  • Architect a centralized project management system and Single Source of Truth, consolidating Asana, Monday.com, Google Sheets, and Slack into an integrated, automated workflow
  • Design and implement automated handoffs between the Ads and SEO departments to eliminate manual follow-up and dropped tasks
  • Audit and redesign fulfillment systems to ensure client deliverables are executed consistently without CEO oversight
  • Build and maintain SOPs across all departments, ensuring teams follow documented processes without reminders


Team Leadership & Accountability

  • Build a culture of radical ownership with team members execute their responsibilities without needing to be reminded
  • Train and develop department managers to lead their teams autonomously, reducing dependence on escalation
  • Implement accountability structures and SOP compliance systems that hold specialists to consistent performance standards
  • Recruit, onboard, and manage team members effectively as the agency scales


Strategic Planning & Capacity


  • Forecast labor capacity around seasonal peaks (spring pressure washing and winter Christmas lights seasons), ensuring the fulfillment engine doesn't break under increased volume
  • Build scalable hiring systems to support 10–20% revenue growth this year
  • Translate the CEO's high-level vision into executable plans and team-ready deliverables without requiring hand-holding
  • Establish executive-level dashboards tracking key metrics such as LTV, cost per acquisition, team productivity


CEO Partnership & Communication

  • Serve as the primary communication filter between the CEO's high-level directives and the frontline team
  • Assertively manage up — enforce boundaries that keep the CEO out of daily Slack channels and day-to-day quality control
  • Prepare clear visual company status reports that remove stress from the executive team
  • Ensure the CEO can permanently focus on organic lead generation, sales, and strategic vision


REQUIREMENTS

Experience (Non-Negotiable)

  • Proven track record as an operator in a digital marketing agency or high-volume service business — you've built this kind of fulfillment system before
  • Experience managing distributed remote teams and driving accountability without micromanagement
  • Background in systems architecture: you've built centralized PM systems, automated workflows (Zapier, etc.), and integrated fragmented tools into a true single source of truth
  • Demonstrated ability to develop managers — you've trained team leads to run their departments independently
  • Experience with seasonal or high-volume client models and the capacity planning that comes with them


Core Competencies

  • Systems architecture and automation — expert-level proficiency with project management tools and workflow automation
  • Data-driven leadership — able to build executive dashboards and govern teams through metrics, not gut feel
  • Change management — proven ability to roll out new processes to teams who've operated on informal systems
  • Capacity planning — experience forecasting labor needs and building scalable hiring infrastructure
  • Exceptional project management skills with an eye for what falls through the cracks


Critical Soft Skills (Deal-Breakers)

  • Thick skin and high emotional intelligence — you can receive direct, blunt feedback professionally and translate it constructively for others
  • Assertive upward manager — you are comfortable (and confident) telling leadership to stay out of the daily weeds when necessary
  • Proactive translator — you take high-level, unfinished directives and independently build the roadmap to execute them
  • Radical ownership mindset — you hold yourself and your team to high standards and don't wait to be asked twice
  • Candid and direct communicator with strong interpersonal, verbal, and written communication skills in English


Mindset & Cultural Fit

  • You thrive in fast-moving, imperfect environments and don't need everything defined before you can take action
  • You're a self-starter who manages your schedule, your team, and your deadlines without direct supervision
  • You're data-driven and make critical decisions based on evidence, not narrative
  • You hold yourself accountable to the highest standards of performance and are resilient in the face of obstacles
  • You see fragmented systems and accountability gaps as opportunities, not liabilities


BENEFITS

  • Salary Range is $100,000 to $130,000 commensurate with experience
  • Role Type is Full Time 1099 Contractor Remote
  • You will also get 15 days of paid time off your first year, and an additional day off each year you are with the company. Personal paid time off is prorated depending on your start date based on the time of year. Paid time off is for both sick days and other personal days.
  • You will also get paid holidays each calendar year. The standard holidays are New Year's Day, Good Friday, Memorial Day, Independence Day, Labor Day, Thanksgiving, Black Friday, and Christmas Eve to New Year's. (We're closed the final week of the year.)
  • Professional Development: This role will be supported by an external Ops program that includes Ops mentorship, community, and live coaching.


HOW TO APPLY

If you are interested in this position, please submit an application at the following link.


https://eltiunaqqfh.typeform.com/to/ZDyoUcki


Our team will review your application and get back to you shortly. We look forward to hearing from you!


DISCLAIMER: SpyGlass Ops is an authorized representative of Creatively Innovative. We are an Operations Hiring Agency, working on behalf of startup businesses to find and hire Operations Positions. All of our roles are full-time, salaried, leadership positions within growing businesses. We also filter the businesses we work with, to ensure they provide long-term positions, growth opportunities, and a strong working environment / culture. Our company qualifies and interviews candidates, then connects finalists with our clients for final interviews and job offers. Our highest priority is creating win-win matches for both our candidates and clients.