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AI & Automation Systems · Founder, Recess Cleveland · Columbia Engineering ’06

SYSTEMS IN. OUTCOMES OUT.

Alexander Robertson — full-body 3D avatar in fedora, glasses, vest, and boots

AI workflows, CRM automation, and agent systems for lean teams — designed, built, and trained in, so your team gets hours back every week.

Founder, Recess Cleveland · Columbia Engineering ’06 · Systems running live every day

Hi, I’m Alex.
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Cleveland, OH
★★★★★

Backed & recognized by national & Cleveland leaders

  • Dick's Sporting Goods
  • Nike
  • Goldman Sachs 10,000 Small Businesses
  • Cleveland Cavaliers
  • Mandel Foundation
  • Cleveland Magazine

WORK WITH ME

Ways we can build.

02 2–4 WEEK BUILD

Automation Sprint

Designed, built, tested & handed off

2–4 week build. I design, wire, and ship your highest-leverage AI workflows (CRM, lead follow-up, ops routing, reporting, content engine) and train your team to run them.

  • Built on the right AI model and tools for the job — selected per project, in accounts you own
  • End-to-end testing, guardrails & error alerts
  • Live team training + written operating playbook
03 ONGOING · LIMITED TO 2–3 TEAMS

Fractional AI Operator

Monthly systems architecture & iteration

Ongoing monthly partnership for 2–3 select teams at a time — continuous workflow shipping, agent tuning, and systems leadership without hiring a full-time head of AI.

  • New automations & agents shipped every month
  • Direct Slack/async access & bi-weekly ops reviews
  • Proactive monitoring, prompt tuning & stack upgrades

SPECIALIZED SYSTEMS & ENABLEMENT

Focused builds & team adoption.

Deployable as standalone engagements or layered into an Automation Sprint — built inside accounts your organization owns.

04 PIPELINE ENGINE · CLIENT-OWNED

AI Lead Generation & Outbound Systems

Done-for-you outbound engine

Warmed sending infrastructure, prospect enrichment, sequenced multi-touch outreach, and replies routed straight into your pipeline. An outbound engine you own — not rented leads.

  • Dedicated sending domains, inbox warmup & deliverability guardrails
  • Targeted prospect list building, data enrichment & AI personalization
  • Multi-touch outbound sequences with positive replies routed to your CRM
05 LOCAL & SERVICE GROWTH

Reputation & Reviews Automation

Automated review capture & response

Automated review requests after every job or visit, AI-drafted responses for owner approval, and instant alerts when a damaging review lands.

  • SMS & email review requests triggered automatically post-visit or post-close
  • Voice-matched AI response drafts queued for 1-click owner approval
  • Real-time escalation alerts for low ratings before momentum stalls
06 NONPROFITS · UP TO $10K/MO GRANT

Google Ad Grants Management

501(c)(3) search grant activation & management

Setup, reactivation, and full management of the up-to-$10K/month donated search ads program for eligible 501(c)(3) nonprofits, including compliance upkeep and converting landing pages.

  • Eligibility audit, initial grant application, or lapsed account reactivation
  • Mission-aligned keyword architecture, conversion tracking & landing pages
  • Ongoing monthly compliance management so your grant stays active
07 STANDALONE OR SPRINT ADD-ON

AI Team Training & Adoption Workshops

Live workshops & role-specific playbooks

Role-based hands-on workshops and custom prompt playbooks built from your team's real work so adoption actually sticks.

  • Live interactive sessions built around your team's actual daily workflows
  • Custom prompt libraries, SOPs & governance guardrails per department
  • Available as a standalone workshop or paired with any Automation Sprint

Built for: Nonprofits, service businesses, and founder-led teams (5–50 people) ready to replace manual busywork with durable AI systems. Every system: Deployed inside accounts you own, with live team training and written SOPs.

SELECTED WORK

Things I’ve built.

01 LIVE CASE STUDY

RecessOS

AI Operating System · Flagship Case Study · Live Daily

The AI operating system I built to run a nonprofit like a company 5x its size: 100-seat AI workforce, nightly self-healing QA, sponsor pipeline, scorecard. This is the case study.

02 Nonprofit

Recess Cleveland

Founder & Executive Director · 2015–Present

Founder & executive director since 2015. Active, healthy, connected communities through play; 8,300+ attendees in 2019 alone — powered behind the scenes by RecessOS.

03 Play HQ

recessROOM

4806 Hamilton Ave, Cleveland · 12,000 sq ft

12,000 sq ft indoor play HQ, 4806 Hamilton Ave, Cleveland. Automated booking, reminders, field trips, birthdays, and leagues.

04 Consultancy

Loud Crayon

AI Workflows, Brand Strategy & Growth Systems · 2008–Present

18 years of brand strategy, SEO, content, and automated operating playbooks for lean businesses — now focused on AI Systems Audits and Automation Sprints.

05 Social Enterprise

Lawn Life Cleveland

Executive Director · 2016–2018

Executive director 2016–2018. A social enterprise whose earned income funded youth workforce programming.

06 Youth Program

Cleveland Youth Landscaping

Co-Founder & Program Director · 2013–2016

Co-founded 2013. Free landscaping for Glenville neighbors; taught youth entrepreneurship and financial literacy.

THE STACK

How I build leverage.

Model-agnostic by design — I work across the leading AI platforms and choose the right model and tools per project, deployed inside accounts you own.

01 AI
Ar
AI Reasoning & Agents
Decision engines, drafting & SOPs
02 AI
Mm
Multimodal AI
Voice, vision & document intelligence
03 AI
Wp
Workflow Pipelines
Multi-step webhook & API orchestration
04 AI
Cb
CRM & Booking Systems
Pipelines, SMS/email & calendar ops
05 AI
Ag
Autonomous Roles
Drafts-first & human-in-the-loop agents
06 AI
Or
Operations Routing
Lead, sponsor, donor & intake sync
07 AI
Ph
Pipeline Hygiene
Automated follow-up & speed-to-lead
08 AI
Ge
GEO / AI Search
Visibility in AI answer engines
09 AI
Vo
AI Voice Agents
Answers, qualifies & books by phone
10 AI
Dm
AI Chat & DM Response
Drafts-first replies across chat & social DMs
11 AI
Ma
Multi-Agent Team Design
Role-based AI workforces that run daily ops
12 AI
Db
Data Dashboards & Scorecards
Live KPI boards & automated reporting
13 AI
Dc
Proposal & Document Automation
Proposals, NDAs & decks generated from templates
14 AI
Ri
Research & Competitive Intelligence
Deep-dive reports on markets, rivals & funders
15 AI
Lb
List Building & Data Enrichment
Prospect lists built, cleaned & enriched
16 AI
Qa
Systems Monitoring & QA
Nightly checks & self-healing workflows
17 MKT
Br
Brand Strategy
Positioning & offer architecture
18 MKT
Ct
Content & Copy
Voice-locked content engines
19 MKT
Em
Email Campaign Automation
Sequences & follow-up that send themselves
20 MKT
So
Social Media Content Systems
Calendars & repurposing pipelines
21 MKT
Vd
Video & Podcast Production
Script-to-publish media workflows
22 MKT
Mb
Membership & Community Systems
Tiers, onboarding & engagement loops
23 DES
Wb
Web Systems
Conversion architecture & custom web
24 OPS
Pt
Partner & Ops Playbooks
Team training & handoff SOPs
25 OPS
Kb
Knowledge Bases & SOP Systems
Shared vaults teams & agents actually use
26 OPS
Gr
Grant Research & Writing
Prospect research & application drafting
27 OPS
Sp
Sponsorship & Partnership Development
Prospecting, decks & outreach sequences
28 OPS
Ev
Event & Booking Operations
Booking, reminders & follow-up on rails

AI Reasoning & Agents

Agent orchestration, complex drafting & operating playbooks

Workflow Pipelines

Multi-step API & webhook automation across your tools

CRM & Booking Systems

Funnels, pipelines, SMS/email sequences & calendar ops

Design & Content Ops

Fast campaign creative, brand systems & partner decks

THE PATH

From circuits to playgrounds — and the AI systems behind them.

  1. 2006

    B.S. Computer Engineering, Columbia University.

    Started in systems thinking, hardware/software architecture, and engineering discipline in New York.

  2. 2008

    Founded Loud Crayon.

    18 years of brand strategy, SEO, content, and automated operating playbooks for small businesses.

  3. 2013

    Co-founded Cleveland Youth Landscaping.

    Free landscaping for Glenville neighbors; taught youth entrepreneurship and financial literacy.

  4. 2015

    Founded Recess Cleveland.

    Active, healthy, connected communities through play.

  5. 2016–2018

    Executive Director, Lawn Life Cleveland.

    Social enterprise funding youth workforce programming through earned income.

  6. 2019

    8,300+ Recess attendees across Cleveland.

    Neighborhood pop-up play, school recess programs, and citywide community activations.

  7. 2020

    The COVID-19 pivot.

    When COVID-19 shut down in-person play, redesigned 40 of 75 games for social distancing and distributed 17,000+ play items and 3,100+ meals; 800 kids played free.

  8. Aug 2023

    Warehouse hit by August 2023 tornado.

    The Recess Cleveland warehouse was struck by a tornado in August 2023 — forcing an immediate operational rebuild while sustaining community programming.

  9. 2024

    The recovery pivot.

    Spent 2024 recovering from the August 2023 warehouse tornado — rebuilding operations and inventory from the ground up, which catalyzed the next pivot into permanent indoor space and scalable systems.

  10. 2023–2026

    National grant & growth recognition.

    Nike "Until We All Win" grant recipient (2023); Goldman Sachs 10,000 Small Businesses graduate (2024); Dick’s Sporting Goods grant recipient awarded to promote inclusive play (2026).

  11. Now

    Building technology for scalability — RecessOS & AI systems as the growth engine.

    Building technology for scalability: running the 12,000 sq ft recessROOM (4806 Hamilton Ave, Cleveland) on RecessOS — an AI-assisted operating system with a 100-seat AI workforce — as our deliberate growth engine, while partnering with 2–3 lean teams at a time to install custom AI & automation systems.

BY THE NUMBERS

Small inputs. Big outputs.

01
100-seat

AI workforce running RecessOS daily

02
12,000

sq ft indoor play HQ — recessROOM

03
8,300+

Recess attendees in 2019

04
17,000+

play items distributed to kids in 2020

05
3,100+

meals served during the 2020 pivot

06
800

kids played free in 2020

07
11 yrs

running Recess Cleveland

08
18 yrs

running Loud Crayon

Dick's Sporting Goods Grant Recipient 2026 (Inclusive Play) Nike "Until We All Win" Grant 2023 Goldman Sachs 10,000 Small Businesses 2024 Mandel Foundation Nonprofit Leadership Program Cleveland Cavaliers / Monsters / Charge Partner Cleveland Magazine Feature Trust for Public Land WKYC / Kaulig Giving

THE HUMAN

Alexander Robertson standing in front of a greenery wall
SYSTEMS ID · CLE
Alex Robertson ID portrait
ALEX ROBERTSON
AI Systems & Founder-Operator
RecessOS · Recess Cleveland
CREDENTIALS COLUMBIA ’06

Columbia Engineering ’06 · Cleveland, OH · Building AI leverage & community systems

Book an audit →

Always
building.

01

Now building AI-assisted workflows that let small teams punch way above their weight — and taking on 2–3 select build clients at a time alongside Recess Cleveland.

02

Founder-operator. 11 years running Recess Cleveland — thousands of families, hundreds of events, one mission: play.

03

18 years of brand and marketing work for small businesses. Columbia-trained computer engineer. I think in systems.

04

Known for turning small budgets, volunteers, and partners into measurable community results.

What I’m good at in one line:

“Lean team in — mighty output out. Systems do the busywork, people do the mission.”

GOOD QUESTIONS

Before you ask.

I install AI & automation systems for small, mighty teams — and I prove it daily running Recess Cleveland on RecessOS.

SAY HI

Let’s build something.

I take 2–3 build clients at a time alongside Recess Cleveland.

I reply fastest to interesting problems.