Chief Technology Officer (Boca Raton)

Chief Technology Officer

Discount Lots | Remote (South Florida preferred) | Full-time | 

ABOUT DISCOUNT LOTS

Discount Lots makes land ownership accessible to everyday buyers. We buy land across the country, sell it on simple owner-financed terms (think rent-to-own for land), and service every note in-house. Founded in 2019 and headquartered in Boca Raton, FL, we are an Inc. 5000 company.

Technology runs the business: a high-volume sales call center, a customer service and collections team, an acquisitions team buying land nationwide, and an e-commerce website where buyers browse and buy property online.

WHY THIS ROLE, WHY NOW

We are in the middle of a major systems upgrade, moving our CRM from Salesforce to Zoho and our phones to CloudTalk, and we are ready to make AI a core part of how the company runs. We need a technology leader who brings structure and discipline to a multi-vendor environment, finishes what is in flight, and then builds what is next.

This is a project-management-first role. The right person runs every initiative with a written plan, firm dates, and visible status, and then leads Discount Lots into the AI generation. You will report directly to the CEO and have real authority to shape our technology for years to come.

WHAT YOU WILL OWN

1. CRM: complete the Salesforce-to-Zoho migration

• Own the remaining migration plan, data cleanup, and cutover, and set the date Salesforce is retired

• Design lead routing, scoring, pipelines, and automations for sales, acquisitions, and customer service

• Write SOPs and user guides, and train every team on the new system

• Make Zoho the single source of truth that every other system feeds

2. Phones and call center: CloudTalk

• Optimize dialer performance, SMS, voicemail, call routing, and call quality

• Make sure every call, text, and disposition syncs cleanly to the CRM

• Complete our transition off Dialpad, including number porting and historical call and text data

• Bring our outsourced call-center partner onto the same stack

• Define call-center reporting: dials, connects, speed-to-lead, and conversion by lead source

3. AI and automation

• Build and execute a 12-month AI roadmap with clear priorities and measurable outcomes

• Sales: call transcript analysis, rep scoring and coaching, live call scripts, automated CRM notes and follow-ups

• Inventory and listings: AI-assisted pricing and comps, listing descriptions and graphics, property due-diligence summaries

• Customer service and collections: payment reminders, at-risk account alerts, self-serve answers for customers

• Operations: automate manual, repetitive work across every department

• Turn the AI tools individual teams already use into reliable, owned company systems

• Train the team, set AI usage and data policies, and choose the right tools (Claude, ChatGPT, APIs, agents, Zapier/Make/n8n)

4. Data and reporting

• Build reporting leadership trusts, from lead source through sale, call activity, customer service and collections, and inventory

• Own data quality across systems and define metrics so everyone reads the numbers the same way

• Give each department head a live dashboard for their team

5. Website and e-commerce

• Own the website, property listing pages, and lead and purchase flows

• Launch buyer waitlists and improve lead intake and speed-to-lead

• Tracking and attribution: GA4, Google Tag Manager, pixels, conversion tracking

• Site performance, uptime, QA, and monitoring

6. Vendors, stack, and security

• Manage developers, CRM implementers, the phone vendor, and consultants on scope, timelines, acceptance, and budget

• Audit every tool and contract, and consolidate where systems overlap (including project management tools)

• Own security, user access, and system documentation

• Recommend the right mix of in-house and outsourced talent as we grow

HOW YOU WILL WORK

• Plan before you build. Written requirements, scope, acceptance criteria, and a test plan before any project starts. Launches happen after sign-off from the department head.

• Visible project management. One project board with an owner, dates, and status for every initiative, which leadership can check anytime. You keep multiple projects moving at once.

• Proactive communication. A short weekly update: what shipped, what is next, risks, and what you need. Risks are raised early.

• Clear priorities. You run an intake process across departments, set weekly priorities, and protect focus.

• Delegation and accountability. You lead through vendors and contractors, hold them to quality and deadlines, and escalate quickly when something is off.

• Plain language. You explain technical tradeoffs so non-technical leaders can make fast decisions.

• Documentation. Architecture, integrations, and SOPs stay current.

YOUR FIRST 90 DAYS

• Days 1–30, learn and take control: Audit every system, integration, vendor, and contract. Stand up the project board and weekly reporting. Prioritize open CloudTalk issues with the vendor. Document remaining Zoho requirements.

• Days 31–60, deliver: Publish a dated Zoho cutover plan and Salesforce retirement date. Complete the Dialpad exit. Deliver the first leadership dashboard. Present your 12-month technology and AI roadmap. Launch the first two AI workflows.

• Days 61–90, scale: Execute the Zoho cutover. Expand AI across sales and customer service. Consolidate redundant tools. Complete core documentation. Recommend the team and vendor structure.

WHAT SUCCESS LOOKS LIKE AFTER 12 MONTHS

• One CRM and one phone system, fully integrated, with Salesforce and Dialpad retired

• Leadership runs the business from dashboards they trust

• AI workflows in production across sales, customer service, acquisitions, and marketing, saving measurable time

• Every project on a dated plan, with no surprise launches

• A lean, documented tech stack with clear owners and the right vendor and talent mix

WHAT YOU BRING

Required

• 8+ years in technology, including 3+ years leading technology at a sales-driven, high-growth company

• Strong project management: you have delivered multiple concurrent, vendor-led projects on time and on budget

• Led at least one end-to-end CRM implementation or migration

• Implemented a cloud phone or dialer system integrated with a CRM

• Put AI into production in real business workflows, with results you can show

• Hands-on skills (APIs, integrations, SQL, Python or JavaScript), enough to build prototypes and judge vendor work

• Experience leading remote teams and outside vendors

• Excellent written and verbal communication

Nice to have

• Zoho CRM or Zoho One experience

• CloudTalk, Five9, Aircall, or similar call-center platforms

• Background in e-commerce or call-center operations

• Real estate, lending, or loan servicing experience

• PMP, Scrum, or similar certification

THE DETAILS

• Location: Remote. South Florida (Boca Raton area) preferred.

• Reports to: CEO

• Compensation: TBD

• Type: Full-time

TO APPLY

Send your resume with a short note covering two things: (1) one AI project you built and put into real use, and what it changed, and (2) one multi-vendor project you led and how you kept it on schedule.