About

CMO, keynote speaker, podcast host — and I never market a product I can’t demo and understand deeply.

I’m Dave Anderson. Chief Marketing Officer at PointFive, the AI Efficiency OS. Saxton-listed keynote speaker. Host of Tech Seeking Human. Australian, based in Boston.

Bio

Storytelling more than strategy. Clarity over cleverness.

I’ve always believed that to understand people, or technology, you need to get close to how it works. That’s why I build with AI tools daily, host conversations with founders and technologists, and never market a product I can’t demo and understand deeply.

My career has been about building stories that scale: rebranding and repositioning Dynatrace ahead of its IPO (lead writer on the S-1, investor deck, and roadshow), driving platform GTM at Contentsquare, and evangelising enterprise AI at DataRobot. Today I’m CMO at PointFive — where Claude and Claude Code are core production infrastructure for an AI-native marketing team.

I also host Tech Seeking Human, currently focused on the economics of the token: how AI usage is priced, measured and optimised as it becomes the unit of work.

Career arc

Twenty-two years of building marketing engines for technology companies.

Now

Dec 2025 — present · Boston, MA

PointFive · Chief Marketing Officer

Building the marketing function at PointFive — the AI Efficiency OS. Directed communications for the $60M Series B led by Accel, launched the platform and TokenShift at FinOps X, and rebuilt the brand and website (Astro, Vercel, GitHub) to +183% search impressions. Runs an AI-native team with Claude and Claude Code as production infrastructure.

2022–2025

3y 5m · Boston, MA

Contentsquare · VP Product Marketing

Owned platform comms and the “One Platform” narrative. Developed the value-based sales pitch adopted globally by field and partner teams. Launched Contentsquare Sense (AI) — the company's most successful product rollout to date at >80% adoption in a single quarter. Managed a global team of 10+ product marketers. Led analyst relations across Forrester Wave, Gartner Market Guides, and IDC Landscape Reports.

2021–2022

11m · Melbourne, AU

DataRobot · VP Marketing & AI Evangelist

Worked with global and APAC organisations to shape AI strategy and connect priorities to real ML outcomes — especially in FSI and retail. Opened C-level conversations at regional FSI leaders. Weekly AMA sessions. Continued Tech Seeking Human throughout.

2014–2021

7y 6m · Melbourne → London → Boston

Dynatrace · Senior Marketing Director APAC → VP EMEA/APAC → SVP Marketing / CMO

Led Dynatrace's transformation from legacy APM vendor to cloud-native AI-powered SaaS platform, culminating in the NYSE IPO in 2019 — where Dave was lead writer of the S-1 narrative, investor deck, and roadshow story. Transformed Dynatrace Perform from a 500-person event into a 4,000+ attendee global conference, then pivoted to virtual for 30,000+ attendees during COVID. Co-led analyst relations with Gartner, Forrester and IDC — Leader in the Gartner Magic Quadrant every year during tenure.

2006–2014

8y · Sydney / APJ

HP · TSG Marketing Comms → Enterprise Marketing APJ

Eight years across HP Australia and the APJ region — B2B integrated marketing communications, paid search budget management across major APJ markets, regional social media strategy execution, brand execution and campaign deployment for HP Enterprise Business.

Earlier

2004–2006 · Perth / Sydney

Precedent · Oxygen Learning · Agency-side marketing & account work

Started on the agency side — proposals, brand development, communications strategy, workshops and training. Studied at The University of Western Australia (BSc Human Movement, MBA Management).

Around the edges

The projects that keep the main job honest.

Podcast

Tech Seeking Human

Long-form conversations at the intersection of technology and humanity. Currently focused on the economics of the token — how AI usage is priced, measured and optimised as it becomes the unit of work. Guests include Magic Johnson, Marc Randolph, Baratunde Thurston, Hannah Fry, Adam Cheyer, Gene Kim, Tricia Wang and Max Tegmark.

Listen

Music

Two albums, one ongoing project

Wish It All Away (2009) earned 4/5 in the Sydney Morning Herald and had a track placed on ABC drama The Lying Game. These Lies That Divide Us (2023) is out on every streaming platform.

Hear it

Home stack

Home Assistant & UniFi

The passion project — a self-hosted home automation and networking stack, tuned in the evenings. Same slow, satisfying loop of design, build, test, revise that shows up in every other part of the work.

Peloton

Ambassador

Long-time rider and Peloton ambassador. Curated playlists, class picks and thoughts on why the community works.

Follow along

Get in touch

Speaking, podcasts, PointFive, or a cup of coffee in Boston?

Say hello →