PlatformCommand · Scout · Anvil→ Advisory & software · Led by a practicing CISO and CIO
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AboutThe Pylon GroupA letter from the founder

Built by operators,
not observers.

An advisory and software studio led by a practicing CISO and CIO. We put senior operators in the seat, and we build the tools we wished existed when we ran those programs ourselves.

Read the letter →
The CISO seatAcademic health, regulated
insurance, healthcare tech
The CIO seatTechnology and product
at a public company
Still in itPracticing, not
retired into advice
§ 01A letter from the founder

Why we
built it.

Written byDan Costantino, MBA
Founder & CEO
Seats heldCISO, CIO and Chief Product Officer across academic health, regulated insurance, healthcare technology and digital assets
Before thatUnited States Marine Corps, cyber and communications. Delivery leadership across national security and technology consulting firms.

Every security team and every CIO I have worked with has a version of the same complaint about their advisors and their tools. Strategy decks from people who left before the regulator showed up. Software roadmaps shaped by analyst surveys instead of the teams that have to live with the result.

I have spent the last two decades inside the role. As a Marine in cyber and communications. As a delivery leader for several cybersecurity and technology consulting firms. As CISO across academic health, regulated insurance, and healthcare technology. As CIO and Chief Product Officer in digital assets. I have written board memos under regulator pressure, sat through audit fieldwork with regulators on the other side of the table, and signed off on post-incident reports.

Plenty of senior advisors have held the seat at some point. Several software products were started by former practitioners. What is rare is finding the same operator working the strategy deck, the audit defense, and the product roadmap, all three at once.

Pylon is built around that overlap. Advisory and software, on purpose, because the practitioner's view comes from the place where the two meet.

The advisory side embeds CISO-level and CIO-level operators into mid-market and PE-backed companies. The software side ships the tools we wished existed when we ran those programs ourselves: Command for the operating picture, Scout for continuous third-party risk, and Anvil for M&A and acquisition diligence.

The two sides talk to each other on purpose. Advisory engagements feed the product roadmap. The product roadmap keeps the playbooks honest. Every feature in Pylon's software shipped because something was missing while we ran a real program. Every advisory playbook gets sharpened by what the software is teaching us in production.

If you have worked with consultants who left before the work got hard, or with platforms that were clearly designed far from the team running the program, we should talk.

Dan Costantino Dan Costantino, MBAFounder & CEO, The Pylon GroupCISSP · CEH · CCNP · CISM
§ 02The thesis

Where advisory
and software meet.

Most firms pick a lane. Advisors advise, vendors build. We do both deliberately, because the practitioner's view comes from the overlap.

Advisory that does not exit at the proposalMost firms advise and leave. We embed and stay. Senior practitioners in the room when the regulator calls, the audit committee meets and the board memo gets written. No partner-to-associate handoff.
Software that respects how programs actually runEvery product exists because something was missing while we ran the program ourselves. We do not ship features that score well in analyst surveys. We ship what gets the work done before Monday's audit committee.
One operator's desk, two outputsAdvisory engagements feed the product roadmap. The product roadmap feeds the advisory playbooks. Each side gets sharper because the other keeps it honest.
Practical over impressiveWe build for the team that has to run the program, not for the deck that has to sell it. Practical workflows, clean reporting, and the fewest moving parts that reach the right outcome.
§ 03The studio

One practice.
Three products.

Shaped by the same operator's hand and held to the same practical bar.

Advisory

Pylon Advisory

Embedded CISO, Embedded CIO and GRC program management. Senior practitioners in the seat, owning strategy, board reporting and the technology decisions that follow.

See services → Command

The operating picture

Strategy, controls, findings, projects and risk on one record that stays current, with Hudson reading across all of it.

Explore Command → Scout

Continuous third-party risk

Assessments read by an AI analyst, a trust network vendors maintain once, continuous external monitoring, and the supply chain mapped past the first tier.

Explore Scout → Anvil

Diligence, priced

Document intelligence, control-by-control assessment and the diligence workflow deal teams actually run, ending in a number the committee can defend.

Explore Anvil →
§ 04Next

A conversation,
not a sales call.

Tell us what is on your plate: advisory, software, or both. We will tell you whether Pylon is the right fit, and what the first ninety days would look like if it is.

See the software →