Career Opening: Director of Delivery at Established Digital Marketing Agency
Full-Time Director of Delivery for a 100% Remote Agency: Own the Technical Infrastructure, Lead a High-Performing Team, and Scale Our Delivery Engine from $3M to $5M+
If you’re a digital agency veteran who loves leading a high-performing team, contributing to innovation, and want to help scale a $3M agency to $5M+, the Director of Delivery position at Ramblin Jackson may be a fit for you. This is a managerial level position with equal parts People Work (managing the in-house employees and vendors) and tech (WordPress, HighLevel, digital marketing, processes) at an established 17-year-old direct response marketing agency.
Watch this video to learn more about the Director of Delivery position before you apply.
Compensation
Year 1 Total Compensation Target: $125,000 to $135,000 + benefits
Base Salary: $95,000 to $105,000
Year 1 Total (Base + Quarterly Bonuses): $125,000 to $135,000 + benefits
Year 2+ (including Profit Sharing): $135,000 to $150,000+
Quarterly Performance Bonuses:
based on Gold Standard delivery metrics, Lead Wrangler rollout milestones, and special project completion.
Entrepreneurial Pay Plan:
Profit-sharing tied to company net profit, starting at 12 month of employment
Career Path: Leadership Team Track: The Director of Delivery is eligible for the Ramblin Jackson Leadership Team at the appropriate milestone.
Director of Delivery Job Description + Key Accountabilities
Where we’re at
We’ve grown to $3M by doing excellent work for Hell Yes Customers: full-service landscape and snow companies across the US who trust us to build their websites, run their SEO, launch their Google Ads, and now manage their leads through our proprietary Lead Wrangler platform.
Where we’re going
We’re on a clear path to $5M — and the Director of Delivery is the person who gets us there.
Can you help us get there?
This is a Leadership Team-track role with real ownership, real compensation, and a real seat at the table. If you’ve been the most capable person in the room at your current agency but haven’t had the authority to match — this is the role you’ve been waiting for
I’m the CEO of Delivery Excellence + Scalability
As the Director of Delivery at Ramblin Jackson, you completely own the quality, timeliness, and scalability of every client deliverable we produce. Your leadership ensures that when a client works with Ramblin Jackson, the work simply works—on time, on brand, and to the Gold Standard.
You are not a people-pleaser. You are a commanding, technically fluent director who triages problems fast, deploys the right people and partners to solve them, and holds everyone—internal Ramblers, trade partners, and vendors—accountable for results. You understand WordPress, GoHighLevel (our Lead Wrangler platform), AI systems, hosting infrastructure, Google Ads, and email deliverability well enough to direct experts and know when something is broken, who should fix it, and by when.
Your ultimate purpose is to help Ramblin Jackson scale from $3M to $5M and beyond—not by doing more yourself, but by building the systems, partner relationships, and team capable of delivering more, better, faster. You are the person our CEO calls when the agency is on fire. More importantly, you are the reason the agency rarely catches fire in the first place.
Key Accountabilities
I am accountable to our Clients, Ramblers, and Ramblin Jackson for:
- Client Deliverable Quality & Timeliness
Ensuring every deliverable—websites, SEO, Lead Wrangler setups, social media, Google Ads—meets the Growth Plan Gold Standard with minimal rework. You own final accountability for quality control and the systems that make quality repeatable.
- WordPress Development & Technical Infrastructure
Owning our WordPress delivery ecosystem—including our in-house Senior WordPress Developer, Account Coordinators, and outsourced development trade partners. You manage resource allocation between in-house and outsourced capacity, ensure the team is not bottlenecked on a single developer, and maintain the technical health of client websites (hosting, security, SMTP, malware response).
- Lead Wrangler (GoHighLevel) Ownership & Rollout
Taking full ownership of the Lead Wrangler platform—our white-labeled GoHighLevel product—including its onboarding process, A2P compliance, technical issues, and the working relationship with our partner Growthable. You will build clear, cohesive processes between Landscape Marketing Guides, Account Coordinators, and the platform itself so clients experience a smooth, professional rollout—not the clunky, delayed experience we’ve had to date.
- Fire Chief — Technical Crisis Direction
Serving as the go-to crisis director when technical emergencies arise—SMTP failures, hosting outages, malware, platform issues. You triage fast, deploy the right internal or external resources, communicate proactively with affected clients, and resolve the issue without escalating to Jack. You will co-create a documented Emergency Response Process with Jack to make this systematic.
- Delivery Process + AI Systems Development & Maintenance
Your job is to scale Ramblin Jackson by first comprehending our current processes, and then directing an AI-first process overhaul across the agency—including Claude Skills, AI agents, and automation tools—and overseeing other Ramblers who build and maintain them. You ensure our AI infrastructure is functional, current, and strategically expanding, including the maintenance and updating of processes. Long-term, you will help position Ramblin Jackson to offer AI development services in partnership with our AI/Dev vendor.
- Trade Partner Management (Development & Production)
Managing relationships and performance of our key delivery trade partners—including web development and HighLevel vendors, Virtual Assistants, and video vendors. You hold partners to deadlines and quality standards, escalate and replace underperformers, and continuously evaluate whether our partner mix is right for where RJ is going.
- Production Team Leadership & People Development
Hiring, coaching, managing, and retaining A-Players on the delivery team—including the WordPress Developer, Account Coordinators, SEO Strategist, Client Fulfillment Lead, Project Manager, and Strategic Operations Specialist. You hold weekly 1:1s, deliver honest feedback, coach B Players up, and remove C Players and Toxic Players without delay or avoidance.
Your Place On The Team
The Director of Delivery reports directly to CEO Jack Jostes and works in close alignment with the Operations Manager and Director of Client Strategy — holding healthy tension with the client strategy side to ensure what gets sold can actually be delivered at the Gold Standard.
Rambler Management — 5 to 10 Direct Reports
You will directly manage the following Ramblers (currently 5 direct reports, growing as RJ scales):
- Client Fulfillment Lead
- Strategic Projects Manager
- Lead Account Coordinator
- Account Coordinator
- Senior Local SEO Strategist
Vendor & Software Management
You own the performance and relationships of our key delivery vendors and software tools:
- Web development vendor agency
- Video editors (freelance)
- Graphic designers (freelance)
- Google Ads vendor agency
- Future: Social Media content and Meta Ads
- Software vendors — Hosting, Review Management, SMTP
- WordPress plugins
- AI tools
Meetings
- Company Meeting — Attend
- Client Strategy Meeting — Attend
- Accounts Department Meeting — Lead
- Projects Department Meeting — Lead
- Weekly 1:1s with all direct reports + Quarterly Coaching Calls
You May Be a Good Fit For This Role If You Are:
Directive, Not Passive — You triage fast, assign ownership, set deadlines, and communicate without being asked. When there’s a crisis, you run toward it.
Technically Fluent — You understand WordPress infrastructure, GoHighLevel or similar CRM platforms, hosting environments, SMTP and email deliverability, Zapier/Make integrations, and AI systems well enough to direct experts and know when something is broken.
A Strong People Manager — You’ve managed developers, SEO specialists, or technical teams. You hold 1:1s, deliver honest feedback, coach B Players up, and remove underperformers without delay.
Accountability-Driven — You hold peers, direct reports, and vendors to deadlines and quality standards. You don’t soften feedback to preserve relationships.
A Scale-Minded Systems Builder — You look at 100 clients and ask: how do we serve 200 without burning out? You build through SOPs, AI tools, automation, and trade partners — not by doing everything yourself. You’re uncomfortable being the single point of failure.
An Integration Architect — When a client uses GoHighLevel for leads and Jobber for field ops, you know how to connect them, who owns the connection, and what to do when Zapier breaks at 9pm.
An AI Enthusiast — You actively use AI in your daily work, follow emerging tools, and help your team adopt new technology even when change is uncomfortable for them.
Hungry for Ownership — You want a leadership seat with real authority. You’re motivated by building something that matters — not just managing what already exists.
What's Hard About This Role:
You Inherit Existing Relationships and Systems You’ll be managing people who have been peers or near-peers, who are excellent at their craft and have been here a long time. Establishing authority with respect, not force, takes intentionality.
GoHighLevel and Integrations Are Real Problems That Need Real Solutions Our Lead Wrangler platform (white-labeled GoHighLevel) has had a rocky rollout. On top of that, integrating GHL with our clients’ field service CRMs — Aspire, LMN, Jobber — via Zapier is a growing challenge with no clean owner right now. You’ll build that ownership model.
You Are the Fire Chief When a technical crisis hits — SMTP failure, hosting outage, malware, broken Zapier zap — you own the response. Triaging fast, communicating proactively, and resolving effectively requires both technical fluency and calm under pressure.
Remote Work This is a 100% remote position with significant Zoom presence. You’ll manage a distributed team and external trade partners across time zones.
Rapid Change AI is evolving faster than any org chart can predict. You’ll need to guide the team through adoption of new tools, new processes, and new ways of working.
Leadership Style: We follow EOS from the book Traction by Gino Wickman. Along with EOS our leadership style pulls it's framework from Five Dysfunctions of a Team and The Ideal Team Player by Patrick Lencioni.
We want people who are Humble, Hungry and Smart -- who are willing to Rumble, which means they embrace respectful conflict and conversation as a means to solving problems.
Who This Role Is NOT A Fit For:
If you avoid conflict or soften difficult feedback to preserve relationships, this role will put you in situations you’re not equipped for.
If you are a "creative agency" or "brand agency" enthusiast -- we are a direct response marketing agency focused on measurable results. Check out our portfolio and case studies on the Clients Page before you apply. If our portfolio isn't your design flavor, and you don't care about the results -- probably not a fit.
If you cannot hold peers, direct reports, or vendors accountable for deadlines and quality, the production team will not respect your leadership.
If you are not technically fluent in WordPress, HighLevel, hosting infrastructure, or software integrations, you will not be able to triage and direct the right resources in a crisis.
If you are resistant to AI, automation, or rapidly evolving technology, you will fall behind in this role within months.
If you build systems that depend on you personally, you will create the exact bottleneck this role exists to eliminate.
If you expect a fully defined, stable environment, this is a role where you will be building the systems as you run them.
Take The Next Steps In The Hiring Process:
- Apply Online in the Form at the bottom of the page
- 20-Minute Interview with Recruiting Manager
- Interview with COO
- Personality Assessment + Skills Assessment
- Interview with Departments Manager
- Final Interview with CEO
- Background Check + Employment Agreement
The Top Three Reasons to be a Rambler:
Grow Your Craft: With a strong focus of personal and professional development through ongoing coaching and mentorship, the Annual Ramblin Retreat in Colorado, the Book Club, and more, we live our Core Value of Craftsmanship in Life and Work, Especially on Fridays. By growing your personal and professional skillsets, you’ll gain more responsibility and grow your income.
Work-Life Balance: Keep your work … at work! Rest well at night with full benefits, job stability, and an accommodating family-friendly schedule. Our 100% virtual/remote empowers our team to do highly focused work from their home office. Note: we do work normal business hours. We close the office from Christmas Eve thru New Years Day each year, and have an accommodating holiday/vacation policy for our team.
Small Business, Big Results: Help Small Businesses Ring The Bell when you exercise creative freedom as an individual and as part of a team to implement the best digital marketing solutions for small businesses.
Advance Your Career with Ramblin Jackson: Culture, Leadership, Collaboration, & Advancement
Ramblin Jackson's Core Values
Our Mission
You won’t be anonymous at Ramblin Jackson. You’ll get to do great work, collaborate with other top performers, and make a real difference in small businesses across the US.
Required Technical Skills
- 5+ years of experience managing complex projects with multiple deliverables, stakeholders, and deadlines. Experience in a marketing agency or digital marketing environment is preferred.
- 3+ years of experience in a digital marketing role with a strong understanding of branding, sales positioning, SEO, and online lead generation.
- 3+ years of experience working with WordPress. Must be comfortable making content updates, communicating changes with the dev team and ensuring quality. Experience with Beaver Builder a plus.
- Understanding of the web development and launch process required.
- Experience with direct response marketing and an understanding of how it all works together (multi-touch, multi-media marketing)
- Experience creating or managing SEO-driven content strategies, including long-form content, service area pages, and Google ranking optimization
- Experience managing Google Ads campaigns, including structuring campaigns, optimizing for conversions, understanding landing pages, and managing ad spend.
- Must be able to clearly explain marketing strategies, project timelines, and digital marketing concepts to business owners and internal teams.
- Comfortable using tools like Asana, Google Workspace, Fireflies.ai, ChatGPT (and other AI tools) and other project management and marketing software to manage workflows and ensure task completion.
Other Required Skills
- Empathy for others + relationship management skills
- Team collaboration skills + ability to give and receive constructive criticism
- Strong written communication skills (you WILL be reviewing web copy)
- Capacity to manage high stress situations
- High level of professionalism + attention to detail
- Incredible time management skills
- Ability to multitask + prioritize work schedules
- Enthusiasm for helping local small businesses in the US, particularily landscapers and others in the green industry
ramblin Perks + Benefits
- 4-Day Summer Workweeks - 12 paid Mondays off in June, July, and August.
- Cash Money - Employee Profit sharing after 1st year. Some positions have additional regular bonus opportunities.
- Paid Winter Break - Our office is closed from approximately the day before Christmas Eve through New Year’s Day, depending on the calendar.
- 5 Paid Holidays - Memorial Day, Independence Day, Labor Day, Thanksgiving Day, day after Thanksgiving.
- Paid Vacation (2 weeks, with 3 weeks after three yers)
- Paid Sick Days (3 days)
- Paid Volunteer Days (1 day per quarter)
- Health, Dental, and Vision Insurance - Insure yourself with options to insure your spouse and your children with our 50% employee + dependent health benefit match with dental and vision options. We offer different options for quality insurance including HSAs, PPOs, FSA, and HMO options.
- Paid Parental Leave - See Employee Handbook for details.
- Short/Long Term Disability Insurance - Options for Parental Leave add-on. See Employee Handbook for details.
- 100% Virtual! - Work from home.
- Normal Business Hours - We work normal business hours -- 8am to 5pm MDT with a one hour lunch break. Flexibility for Ramblers in other time zones.
- Ramblin Jackson University - Learn new skills and onboard quickly with Ramblin Jackson’s online training program.
- Beef Jerky Club - Each week, Ramblers nominate and praise team members who are living the Core Values. Get nominated the most in a month and win a $200 prize. Get the most nominations in a quarter and you get to keep Barry the Bull trophy for the following quarter.
- Book Club - Learn new business skills as you read a premium business book that the team reads together.
- Ongoing Professional Development - Weekly/bi-weekly coaching meetings including employee work/life balance coaching
- Hardware - We’ll provide a current, up-to-date Mac laptop
- Sweet Software - Get your job down with ease using great software! Whoaaa nelly!
Other Requirements
Because this is a virtual position, having a strong on-camera video presence is essential to establish trust and credibility. While this is a work-from-home position, we expect you will dress (for video meetings) as if you were meeting a high-end client in person.
- A Meeting Room - Must have a presentable home office that looks Professional in Video Conferences. A Meeting Room should be a neatly organized room without a lot of backlight, clutter, or things that would distract from the sale. Ramblin Jackson will provide a webcam, lighting, backdrops, and other audio/video equipment as needed.
- Professional Wardrobe and Appearance - The Account Manager must present him/herself accordingly with business casual attire while attending video conferences, in-person meetings, or events with clients.
All applicants are considered for all positions without regard to race, religion, color, sex, gender, sexual orientation, pregnancy, age, national origin, ancestry, physical/mental disability, medical condition, military/veteran status, genetic information, marital status, ethnicity, alienage or any other protected classification, in accordance with applicable federal, state, and local laws. By completing this application, you are seeking to join a team of hardworking professionals dedicated to consistently delivering outstanding service to our customers and contributing to the financial success of the organization, its clients, and its employees. Equal access to programs, services, and employment is available to all qualified persons. Those applicants requiring accommodation to complete the application and/or interview process should contact a management representative.
