Many OSS veterans, the people who built the OSS of today, are no longer being offered full-time roles. Clients often assume they have become obsolete or are simply too expensive.
However, these same experts are still solving the toughest OSS problems, drawing on decades of hard-earned experience. They are just not doing it from inside your org chart.
The real surprise? These highly experienced OSS dragon slayers are often still available, still sharp, and often just one introduction away.
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I received some news last night that really shocked me.
A great client of PAOSS has retrenched an entire division of its workforce, making some very talented OSS experts redundant. Sadly, I’ve been seeing this type of event happening more often over the last few years. It’s clearly a macro trend, so it got me thinking… What can I do to help the people made redundant by this client, but also the many other OSS dragon slayers who have reached out with offers to assist PAOSS in recent times?
Just like our chasm series aimed to find a more efficient integration of OSS Product Buyers and OSS Product Sellers, today’s article explores how to better connect:
- OSS Services Buyers – the organisations that desperately need niche expertise beyond what they currently have within their team
- OSS Services Sellers – the battle-hardened dragon-slayers that are no longer deemed employable, but still have up-to-date and relevant capabilities to share
Unless you’re directly impacted by a redundancy, the macro trend is not a dramatic exit, but a quiet fade from the centre of the OSS stage. I’ve noticed that highly talented, highly experienced professionals, particularly those over 50, who’ve never had any trouble finding jobs in the past are now finding it extremely difficult to find new full-time roles. They’ve survived decades of battling the OSS beast. They’ve seen many architectural / technology pivots, vendors churn, mergers, organisational changes, migrations and much more of course. But now, they’re being seen as too expensive, too close to retirement (ie little tenure runway remaining) or not current enough in their tech knowledge.
Yet OSS is one of the few domains in tech where experience is not just helpful, it’s critical. These veterans built the foundations of the platforms still in use today. They understand the operational reality behind the dashboards, the reasons behind legacy decisions, the transformation project pitfalls and the edge cases that documentation never quite covers. They’ve slayed many dragons on OSS transformations in the past.
Their absence from core teams creates a vacuum. As organisations chase digital transformation, many are unknowingly cutting themselves off from the people most capable of helping them towards successful navigation of the transformation.
And let me be completely clear up-front. I totally understand the need for organisations to transition and evolve their workforce too, so this is not going to be an attack on the employers. Instead, this article will explore the possibilities of how buyers and sellers can serve each other better given the known constraints.
Still Fighting Fires: Why These Experts Are Far from Obsolete
Unlike some tech domains where skills quickly expire, there are two parts to this concern:
- OSS is anchored in systems thinking. It rewards people who have been around the industry long enough to identify and understand patterns, relationships, and operational nuance. Veterans thrive here because the problems are rarely new, they are layered, inherited, or deeply embedded. Patterns of past behaviours, that are often highly nuanced or barely discernable, become easier to identify when the sample size of experience is increased
- More importantly, OSS professionals have always been forced to evolve so the risk of obsolescence is slim. New protocols, cloud-native, hybrid networks, API-first design, AI-driven observability, these veterans have integrated all of it. Their value lies not just in knowledge, but in the judgment to choose when not to act, when to isolate instead of replace, when to patch instead of panic… etc, etc
As technologies improve and more aspects of OSS become “plug and play” the complexity is often abstracted away from the typical OSS user. This is where experienced engineers are often able to decipher the deeper problems due to their experiences BPAP (before plug and play).
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Unclaimed Advantage: Senior OSS Talent Is Available, Just Not Employed
So this is where the contradiction becomes clear: clients still face serious OSS challenges. They still need experts who can handle complexity, both broad and deep. But instead of hiring dragon slayers, they’re hunting unicorns, mid-career generalists who are cheap, current, efficient and have deep understanding of systems / processes.
We’ve possibly also heard of OSS Services Buyers who bemoan the impending talent cliff, whereby their experienced staff are nearing retirement and aren’t easily replaced.
Senior and/or experience talent has not vanished. It has just shifted. Increasingly, these professionals are:
- Freelancers or independent consultants
- Strategic advisors across multiple clients
- Part-time contributors or interim roles
- On-demand troubleshooters
- Off-shore or outsourced due to the procurement trends of recent decades
Let’s look at just a tiny few examples of where these models shine:
- Legacy-modern system transformations where historical knowledge is a major impediment to being able to transition to a desired future state (and most transformations are constrained by imperfect knowledge about legacy current-state)
- Architecture triage when an ongoing project keeps failing to deliver or continually gets gridlocked
- Complex integration or vendor migrations with limited internal documentation
- Security posture reviews where decisions made 10 years ago still matter
In all of these, experienced consultants solve problems faster and more reliably, not necessarily because they’re better, but because they better understand the problem behind the problem and intuitively understand how to unblock legacy challenges.
Their availability is often quite flexible. Their scope is focused. What’s missing is the mechanism/s for connecting OSS Services Buyers and Sellers. This task of building the bridge is worth diving deeper into!!
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Building the Bridge: How PAOSS Can Help Connect Experts and Clients
The PAOSS “Find Experts” initiative has been in place for many years. It aims to assist:
- OSS Services Buyers who are looking for talent
- OSS Services Sellers who are looking to be found
But in all honesty, we haven’t given it as much attention as it deserves. It’s just a very basic service today, with so much untapped potential. The following ideas are just 4 initiatives that PAOSS could launch to strengthen this bridge:
- Client-Expert Matchmaking
This is the basis of the platform today, where a human-assisted pairing process happens based on problem types, not keywords. Could be much better and more sophisticated though - Expert Availability Communities / Boards
A loosely moderated board where OSS experts can communicate to solve problems that is public and becomes trusted - Mentoring Pods and Expert Panels
Regular small-group interactions where veterans support early-career professionals. Not only builds talent pipelines, but also keeps experts top-of-mind. - Job Boards
We already monitor OSS-related jobs across various platforms from around the world, but more as a means of identifying patterns of skills and technologies used in the real world. We don’t have any intention to become recruiters, but we could do a better job of surfacing the available roles as we become aware of them
Where do we go from here?
The macro shift described above will not be solved by a single job board or community though. What we need is a new model for relevance, one that values insight over tenure, outcomes over employment, and contribution over age.
This is where we’d love to hear your thoughts.
- Are you either a buyer or seller in this market
- Do you have any thoughts on how PAOSS can contribute more to overcome this problem
- How have you solved the seller problem after you were laid off
- How have you solved the buyer problem when your in-house team needed help
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The OSS Dragon Slayer Action Plan
We certainly don’t have all the answers but here is a checklist for all sides of the OSS ecosystem.
For Senior Professionals (OSS Services Sellers)
If you’re in this cohort, chances are you’ve never really had to “market” yourself in the past. The skills you’ve shown on a job have been noticed by others and opportunities have just followed you. You’ve probably never actively attempted to build a personal brand other than to update your LinkedIn profile and resume.
But your personal brand, your marketing gravity, has never been more important. It would be great to have started building this years ago though because it is a technique that starts off slow and builds momentum over time. It’s unlikely that you’ll have time to do all of the gravity builders in the chart below, but you might like to pick a few that resonate the most with you. [As a side note, you’ll probably notice that PAOSS uses a few of these techniques including, articles/blogs, monthly meetups, books, surveys, newsletters, special reports, this website, podcasts, YouTube videos and more]
Additionally:
- Create or update your “Find Experts” profile on PAOSS with the type of expertise you’re able to provide
- Turn past wins into short case studies or diagnostic templates published on LinkedIn, YouTube, your Notion page, your website, etc
- Offer public office hours or micro-consulting sessions
- Share insight in open forums, webinars, or commentaries
- Form boutique consultancies or problem-solving pods with peers
- Explore fractional CTO or advisor roles, especially with startups and scaleups
- Start your own company, or this other clever alternative
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For Clients (OSS Services Buyers)
- Create or update your “Find Experts” profile on PAOSS with the type of expert you’re seeking
- Establish training / mentoring programs to enrich the long-term capabilities of your workforce
- Leave us a note describing the problems you’re trying to solve and we’ll aim to connect you with our network
- Pilot small-scope projects with veteran consultants
- Define needs as problems, not roles
- Budget for targeted advisory help in high-risk areas
- Review and adjust internal hiring filters and assumptions
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For PAOSS and the Broader Community
Here are just a few of the types of ideas we’ve considered in the past, but haven’t made it to the top of our to-do lists yet. Maybe there’s some ideas for you to build amongst them:
- Expand the “Find Experts” interface to include richer metadata, filters, and case studies to shine a light on the many talented OSS experts who are seeking to be found
- Add global OSS/BSS job boards to the website
- Trial flexible engagement formats (eg expert pods, asynchronous advisory sprints)
- Collect and publish stories showing where veteran input changed the outcome
- Enable a feedback loop so clients and experts co-design future services
- Host open forums to prototype new models together
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And finally, over to you…
This article is not a final answer. Not by any stretch. It’s merely a starting point.
We know the expertise exists. We have seen the value it delivers. But the mechanisms and systems to connect people to it, at the right time, for the right problem, are still a challenge worth solving (for PAOSS and the broader community).
If you are an expert with a story, a client with a challenge, or a peer with an idea for better engagement, share it. Let us use PAOSS not just to find each other, but to rebuild the OSS ecosystem to better include its most experienced contributors.
The dragon slayers have not disappeared. They are ready. We just need to open the gates and lead them into battle again.