Hi, I’m Jack

I lead Client Strategy & Solutions at Interlaced, and I’m the co‑founder of Scrubbr.ai.

I’ve spent eight years in the technology space. I started as the in‑house IT person at a company that still ran its own Exchange server, and since then I’ve worked with everyone from AI‑native startups to mid‑market companies with 500+ employees.

My work sits where sales, infrastructure, compliance and AI meet. I’ve personally deployed everything I sell, so when I scope something, I know what it takes to deliver it.

See my work Get in touch
Illustrated portrait of Jack Dickinson smiling, wearing a brown t-shirt against a warm tan background
$1.4M+
in non‑recurring revenue closed
$100K+
in monthly recurring revenue added
8 years
working in IT
11
compliance programs built from scratch
50+
people using Scrubbr.ai
Sales

Two years in a quota‑carrying role, and I haven’t missed my number yet

I sell network, security and compliance work at a $4M ARR company. I’ve deployed everything I sell, so I can give customers honest scopes and realistic timelines. I think that’s a big part of why they trust me.

$1.4M+
in non‑recurring revenue from projects, buildouts and deployments
$100K+
in new monthly recurring revenue for a $4M ARR business
Every period
at or above quota over two‑plus years
A few deals I’m proud of

Airport restaurants, AI startups and security rollouts

Some of my favorite deals have been the physical kind, like building networks inside busy airport terminals and setting up new offices for AI startups in San Francisco.

I’ve also sold 14 vCISO engagements and a lot of security software, from everyday email security to complex data loss prevention.

  • Network builds for 10+ airport restaurants
    Full buildouts inside working terminals
    SANDENSFO
  • Office buildouts for AI startups
    Many large offices across San Francisco
  • 14 vCISO engagements
    Fractional security leadership for growing companies
  • Security software deployments
    From email security to data loss prevention
Infrastructure

Eight years in IT, from on‑prem servers to AI‑native cloud

My first IT job was at an old‑school company that ran everything on‑prem, including its own Exchange server. Since then I’ve worked in just about every kind of environment, including AI‑native companies with complex cloud setups and real compliance requirements.

The environments I’ve worked in
Where I started
Fully on‑prem
Self-hosted Exchange, physical servers, everything in‑house
Along the way
Hybrid Microsoft 365
Migrations, identity and a foot in both worlds
Modern teams
Cloud‑first
SaaS‑heavy companies with SSO everywhere
Today
AI‑native
Complex cloud infrastructure with compliance built in

Rack‑and‑stack network deployments

I’ve done full physical network builds, from an empty room to a working network.

SSO and identity rollouts

I’ve moved whole organizations onto single sign-on, so access is simpler for people and easier to audit.

Company‑wide changes

On big changes that touch everyone, I’ve managed the project and done the hands-on technical work.

Compliance

Helping companies through SOC 2, CMMC and HIPAA

I’ve helped 7 businesses go from no program at all to SOC 2 Type 2, one to CMMC Level 2 and three to HIPAA. I’ve worked on policy writing, change control, company‑wide tool rollouts, evidence collection and the audits themselves.

7
SOC 2 Type 2
Businesses I’ve helped go from nothing to Type 2
1
CMMC Level 2
From zero to CMMC Level 2
3
HIPAA
Businesses taken from zero to HIPAA compliance
How I approach it

Controls that fit how the team already works

Auditors look at what a company actually does, not what the binder says. So I try to build controls into the way people already work, and then help show the evidence when the auditor asks for it.

  • Policies written and approved
  • Change control in place
  • Security tools rolled out company‑wide
  • Evidence collected and submitted
  • Audit walkthroughs attended
Right now I’m taking my own startup through SOC 2 Type 1. Our controls are already built to the Type 2 standard, so that’s the next step.
AI

Building with AI

I’m not a developer, but I co-founded a company and used AI to build a real product that people use every day. I’ve also built agents and automations for founders, and at Interlaced I help shape how we bring AI to our clients.

Co-founder

Scrubbr.ai

An enterprise‑grade operating system for your communications. It brings email, chat, calendar and meeting notes into one place and shows you what actually needs your attention. More than 50 people use it today, and that number keeps growing.

Visit Scrubbr.ai
Consulting

Arkand AI

With Arkand AI, I built custom automations and agents for founders who needed to save time or bring in more revenue.

Client Strategy & Solutions

Interlaced

I lead Client Strategy & Solutions at Interlaced. Part of that is shaping how we roll out AI for our clients: choosing the tools we build on and the services we offer, so clients can adopt AI safely and get real value from it.

I’d love to hear what you’re working on

Whether it’s a network build, a compliance program or an AI project, feel free to reach out. I’m always happy to talk.

Email me