Humans in the Loop
About

A running log, not a launch

Humans in the Loop is Bruce Cullen thinking out loud about the AI tools he uses at work — what they did, what they cost, and where a person still has to stay in the loop.

Start with EP 001
HITL
Weekly · 30–45 minutes · Agents, products, governance and the week’s news.
The host

Bruce Cullen is a Director of Products with more than seventeen years across product management, engineering leadership, delivery and quality. He has taken B2B SaaS products from a blank page to product–market fit, led on-prem to cloud transitions, built engineering organisations from one person to seventeen, and owned the roadmap for a portfolio worth around $11m ARR.

Today he runs the product function at WorkspaceDNA, covering application migration, packaging, testing and deployment across the Microsoft estate. That means AI tools meeting real constraints every week — procurement, security review, and people who did not ask for a new workflow. The show is the honest version of that.

No predictions, no hype cycle commentary, no guest chasing. One week of work, reported back.

What you get

Three things, every week

One build
Something actually attempted at work, with the parts that failed left in.
One decision
Where a human had to stay in the loop, and why.
The news
Ten minutes on what shipped and what it means for people who buy software.
Track record

Where the material comes from

Seventeen years of shipping software people pay for, mostly in B2B SaaS, cloud-native and on-prem.

WorkspaceDNA
Feb 2026 — present
Director of Products & Community

The product function across a multi-product line-up for application migration, packaging, testing and deployment on Microsoft platforms. Currently driving a full UX redesign to pull several separate modules into one product, and taking the roadmap out in public as well as around the business.

Eido Software
Feb 2025 — Dec 2025
Director of Products & Founding Member

Zero to one, and product–market fit inside six months, for a reporting and management platform for Microsoft Intune — $1m ARR. Built the engineering organisation from nothing to five, used AI-driven prototyping to shorten discovery, and ran the repositioning that made the product legible to buyers.

SquaredUp
Jan 2022 — Feb 2025
Director of Products, and a year as interim Director of Engineering

Multiple roadmaps across dashboarding, data visualisation and observability — roughly $11m ARR of SaaS and on-prem. Scaled the plugins engineering department to seventeen, built the product team to four, and cut setup for key data sources from forty-odd clicks to five.

Cookdown, a SquaredUp brand
Jan 2019 — Feb 2022
Director of Products & Founding Member

Founded the brand: six products for alert tuning and systems integration across SCOM and ServiceNow, a team of six, $1.5m ARR, one acquisition, and customers including Deloitte and Investec.

SquaredUp
Jan 2018 — Dec 2019
Program Manager

Engineering and project functions end to end: process, Agile transformation, tech previews and the customer feedback cycles behind them.

Citrix
2008 — 2018
Senior Cloud Technical Project Manager, and before that release and test leadership

A global delivery transformation across roughly 450 engineers in five countries: Citrix Cloud moved from irregular multi-month releases to a reliable three-week SaaS cadence, and XenApp/XenDesktop from year-long waterfall to a three-month Agile rhythm. Earlier, built and ran the Test Project Office and its 55 engineers.

Outside the day job

Communities and committees

Atlassian Community Leader
Apr 2022 — present
Founded the Thames Valley community and runs London events as chair and MC, recruiting speakers and sponsors. Holds an Atlassian award for presenting and event quality.
Experts Live UK, co-organiser
Jun 2025 — present
Organising large-scale Microsoft technology conferences — sponsors, speakers, venues.
Holy Trinity Aylesbury, trustee
2020 — present
Secretary, and lead for IT and fabric. Governance, policies, and a major heating upgrade.
Credentials

BSc ICT, first class, Birmingham City University. Agile PM Practitioner, Lean Six Sigma Green Belt, APMP, ISTQB Intermediate — the paperwork behind a long habit of caring how things actually get delivered.

If you want the show rather than the CV, the archive is the better place to start.

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