Enterprise Enablement at Portfolio Scale

Summary

Aspire Software (part of Valsoft) is a portfolio of around 60 software companies that grows by acquisition. I was the enterprise Jira champion for all of them, and the person rotated in to improve processes company by company — standardizing how newly acquired teams onboarded and worked, across wildly different cultures, tools, and maturity levels, with no direct authority over any of them. The lasting win wasn’t doing the work myself; it was productizing it — templates, a repeatable process flow, and a trained specialist team — so enablement scaled across the portfolio without me in the loop.

The challenge

A portfolio that grows by acquisition has a recurring problem: every new company arrives with its own tools, culture, and maturity, and somehow has to join a common way of working. Before I owned this, the only requirement for a newly acquired company was to onboard into the enterprise Jira instance — with little guidance, which meant it easily got messy. Multiply that across ~60 companies spanning the US, Canada, Spain, Sri Lanka, Bulgaria, and Egypt, and the absence of a standard wasn’t a nuisance; it was a tax on every acquisition. And none of these teams reported to me — adoption had to be earned, not ordered.

The work — two strands

Jira enablement across the portfolio. As enterprise champion I supported all ~60 companies on Jira administration, but most of the work came from new acquisitions onboarding to the enterprise instance. If a company already ran Jira, I helped migrate it or guided their local admin through the process; if they didn’t, I trained them, stood up their projects, and applied a standard Jira process flow I’d created. A messy, guidance-free onboarding became a structured one.

Process improvement, company by company. Every few months I was assigned to a portfolio company to review their processes — agile and non-agile — make recommendations to their management, and help implement improvements: development workflows, Gitflow, release processes, and partial agile transformations.

The method — buy-in without authority

Driving change across companies you don’t command lives or dies on buy-in. My rule, borrowed from a mentor: let them eat dessert first. Start with the highest-value, lowest-effort changes — the quick wins that visibly help. That lowers defenses fast, with both team members and management, and earns the credibility to tackle harder things. I paired it with transparency: I was honest that full transformation takes time, and that for now I was solving tactical, short-term problems. Under-promising the timeline while over-delivering early is what turned skeptics into partners.

The multiplier — productizing the work

The result I’m proudest of is that I made myself unnecessary. Jira onboarding became template-led, and I trained a dedicated Jira specialist team to run onboarding for new acquisitions using my templates and process flow — so enablement no longer depended on me personally. On the process-improvement side, the effects showed up quickly: development processes tightened, git strategies shaped up, and botched releases dropped. Turning a one-person champion role into a repeatable system is what let it scale to the whole portfolio.

What I’d take with me

• Productize the work, don’t just do it — templates plus a trained team turned a one-person role into a system that scaled across ~60 companies.
• Lead change without authority by sequencing for trust — high-value, low-effort wins first; honesty about the long road.
• Standardization is how a portfolio scales — a common way of working makes every new acquisition cheaper to absorb.