Fractional CTO / AI Automation Architect for Duke’s Landscape Company - Contract to Hire
We are looking for a sharp, hands on technical operator to help modernize and scale Duke’s Landscape Company.
This is not a basic IT support role, and it is not a generic marketing automation role.
We need someone who can look across our business, understand how we operate, recommend the right tech stack, and build practical systems that improve outreach, follow up, CRM, reporting, internal workflows, and customer experience.
We are a premium landscape design build company focused on higher end residential work and long term referral relationships with builders, architects, interior designers, pool contractors, realtors, and property managers in Northern Colorado.
We already have strong strategy, messaging, process thinking, and direction. What we need now is the right technical person to architect the system behind it and help us implement it the right way.
What we need help with
We want someone who can assess our current stack and improve it in a practical, scalable way.
This includes:
CRM strategy and setup
Lead and partner pipeline design
AI assisted outreach workflows
Email and SMS automation
Meeting booking and follow up flows
Internal dashboards and reporting
Contact management and data cleanup
Workflow automation between platforms
Calendar and communication integrations
Website intake and future portal workflow planning
General AI implementation opportunities across the business
A major focus will be helping us build a referral partner operating system that supports outreach, follow up, fast budgeting or ROM requests, design requests, and eventually a gated partner portal.
What success looks like
The right person will help us:
Recommend the right stack instead of just adding more software
Reduce manual busywork
Build automations that feel natural and practical
Create better handoffs between outreach, sales, estimating, and operations
Make sure the right information is tracked in one place
Set up systems that are scalable and not fragile
Document what is built so our team can actually use it
Phase 1 scope
We expect the first phase to focus on audit, architecture, and MVP implementation.
That likely includes:
Tech stack audit
Review our current tools, workflows, bottlenecks, and gaps.
Systems architecture
Recommend the best stack and map how our CRM, communications, automations, AI tools, and intake workflows should work together.
Referral partner growth system MVP
Build the first working version of a system for partner outreach, follow up, and pipeline tracking.
CRM and data structure
Set up or improve fields, stages, segmentation, reminders, reporting, and visibility.
AI and automation workflows
Build practical workflows for message drafting, follow up logic, meeting prep, notes, and task creation.
Dashboard and reporting
Create a simple view of activity, replies, booked meetings, opportunities, and next actions.
Documentation and handoff
Provide Loom walkthroughs and SOPs so the system is usable after launch.
What we are looking for
We want someone who is both strategic and hands on.
You should be comfortable thinking like a fractional CTO, but you also need to be able to actually build.
Ideal experience includes:
CRM architecture
Workflow automation
AI implementation for small or midsize businesses
Lead management systems
Sales and outreach systems
Data cleanup and enrichment
Reporting and dashboards
Business systems consulting
Helpful tool experience may include:
HubSpot, Close, Pipedrive, Airtable, GoHighLevel, or similar
Zapier, Make, n8n, or similar
Twilio or SMS workflow tools
Clay or enrichment tools
Calendly integrations
OpenAI or Anthropic API workflows
Notion, ClickUp, Monday, or similar internal operations tools
Light portal or front end workflow planning is a plus
Important
We are not looking for a spammer.
We are not looking for someone who throws together messy automations that constantly break.
We want strong judgment, clean implementation, and practical systems that support a premium brand experience.
How to respond
Please include the following in your proposal:
A quick summary of similar systems you have personally built
What kinds of businesses you have done this for
The stack you would recommend for a company like ours and why
How you think about AI implementation in a practical, non gimmicky way
What you would prioritize in the first 30 days
Whether you prefer hourly or fixed price for phase one
Examples, screenshots, Looms, or case studies are very helpful
Screening questions
Tell us about one business where you helped improve the full tech stack, not just one automation.
What would your first three priorities be for a company like ours?
How do you decide what should be automated and what should remain human driven?
What tools would you be most likely to recommend for CRM, automation, and reporting, and why?
Have you built systems that support outbound outreach, follow up, and meeting booking?
Are you personally hands on in the build, or do you mainly advise and delegate?
Project structure
We are open to either:
An initial paid discovery sprint followed by implementation
or
A phased fixed price engagement with clear milestones
We are not looking for a huge agency. A strong solo operator or a very small team is probably the best fit.
About us
Duke’s Landscape Company is a premium landscape design build company focused on creating high quality outdoor environments and building strong long term referral relationships in Northern Colorado. We care about doing things well, keeping communication organized, and creating systems that support real business growth.
To show you actually read this post, start your proposal with:
Duke’s Systems
Current Tech Stack
- LMN (landscape software for estimating)
- Monday
- HubSpot
- Paychex mobile time app
- Various AI tools
- Slack
- Company Cam
- Google Workspace
- AutoCAD
