Retrospective: It Pays to Hold Your Ground

Kent Dahlgren
8 min readJan 2, 2021


This is a tale of stubborn perseverance, and a refusal to follow orders, because I’m pathologically insubordinate, and the direction of executive management is often wrong.

In the technology industry, an endorsement from Gartner is considered a “should buy” from one of the industry’s most respected names

Once upon a time I was a product manager for a company called Tripwire, and this product (Tripwire Log Center) was one of my responsibilities.

A PRODUCT manager is different than a PROJECT manager, btw.

The product manager is responsible for a product’s financial portfolio, and is generally referred to as “the CEO of the product.”

I may not have had anybody reporting directly to me, but I was painfully aware of the fact that the failure of my product meant a large number of people would be unable to pay their bills, and I took my job seriously.

Most executive teams don’t know how to manage product managers, and Tripwire was no exception; I experienced 16 management changes in my six years.

In practical terms this meant that I was constantly re-interviewing for a job I’d had for years, and it was common for a new manager to just lay off a few product managers, for no other reason than to “make their presence known,” replacing them with a couple of their own loyal guys, doomed to be laid off in six or eight months when the next manager comes along.

But I had staying power because it’s my way to volunteer for work nobody else wants, and it’s in this manner that I was given responsibility for the most unpopular product in the company.

This product (Tripwire Log Center) was the first product that Tripwire had acquired, and the post-acquisition “stabilization” period was rocky.

But the product emerged strong and very capable, because thanks to vital support from some great leadership, as well as a vital collaboration with the company’s superb support and finance organizations, I was able to implement a few operational plans I’d learned in the decade I’d invested in global manufacturing companies like Tektronix and Xerox (who acquire shitty products and stabilize them all the time).

For reasons that were at first mysterious, the product was extremely unpopular among the executive team, but not for any reason that could be sourced in data, because believe me: I had the data.

Average sales price improved when the product was used in an integrated configuration, average margins improved, and the product made our solution more “sticky,” meaning it was less likely to be removed — all considered best practices.

But I soon learned that the acquisition had been approved by the CEO’s predecessor, and the CEO at the time didn’t like it.

It’s just that simple.

Time again I’d heard from one senior sales person after another: “he won’t allow it to succeed, no matter what you do.”

Just like that: the product was considered a career killer.

It didn’t matter that the product had dramatically closed the “breach to detect and respond” gap, which meant that hundreds of some of the world’s most important companies (and entities) were able to more capably address the risk of hackers.

It didn’t matter than the R&D team had improved its performance and resilience dramatically, overshadowing the competition.

None of that mattered: any effort to champion on its behalf was a dead-end, regardless of how well the product performed, and regardless of how well the product contributed to the bottom line.

By 2014 my latest boss (number 16) was placing me under tremendous organizational pressure to declare this product “end of life,” which means that we’d effectively close up shop.

But I refused, lending insights into why I ended my 12 years in the military well-decorated, but no more senior than an E-5: I’m all about insubordination when management is wrong.

None of the financial or operational data supported the directive, and ultimately I am more loyal to the company than I am the whims of any particular executive, regardless of how important they think they are.

I mean, I’d experienced 16 management changes, right? The senior executive caste is often dominated by the feckless, and the feckless come and go.

More to the point: I’ve had to lay people off in my life. I can do it, but it doesn’t mean I enjoy the experience, you feel me?

Refusing to give in or give up, I worked tirelessly to demonstrate how the product was actually the company’s salvation.

I was able to repeatedly demonstrate how an inexpensive reconfiguration and repacking of the product would quickly place the company in alignment with massively inorganic growth, placing it in the crosshairs of new markets as they eventually materialized (including “Endpoint Detection and Response” — now a multi-billion dollar industry).

Each attempt was denied, and each time I was ordered to cancel the product.

At best I was told to “edit the presentation format,” which is executive shorthand for “we don’t care about the content of your presentation.”

By summer of 2014 I was being regularly screamed at by my manager, and I mean he was literally shouting at me, demanding that I shut the product down.

HR didn’t really give a shit about this experience. Why would they?

And for context, during this same era we had experienced a miscarriage, followed by the birth of the twins, the youngest of whom almost died soon after birth.

Picture me, at the PICU, taking direct calls from customers who were concerned by rumors of the absurd directive to shut off the product, while watching out of one eye for my youngest daughter to take her last breath.

In general, corporate management doesn’t really care about you or your children, you know? Not even the smallest bit, and it doesn’t matter who you are.

And so after six years, I left Tripwire and joined Tenable (maker of Nessus), managing a couple of their security products (PVS and LCE, as well as their hardware line), and bringing with me some knowledge on the design and management of software agents (Nessus released its agent architecture in 2015)…the same year Tenable received $250m USD in series B funding)

Anyway, that was in 2014. It’s now 2021. It’s been seven years.

It’s seven years since I was ordered to shut down the Tripwire Log Center product.

As you can see, as of this afternoon, the analyst Gartner gives the product an 93% “would recommend” rating; in the security industry, there’s few analyst endorsements that are considered more substantial.

Does that mean Tripwire is still selling their Log Center product?

Yes, of course they are. Duh!

What happened to the executive demands to sunset the product?

No idea, although it would be my supposition that the CEO cashed out and moved on, because many executives negotiate their exit when they are hired.

Does that make sense?

Under ordinary circumstances: the stewards of the organization (the executive caste) have a financial disincentive to embrace risk of any kind, even if it means it may result in inorganic growth.

Which means that ironically, the executives are often the ones most commonly responsible for stifling and even killing innovation from within their own organizations, even if these innovations represent an opportunity for inorganic growth.

What’s preferred is predictable mediocrity, provided the executive caste is able to cash out and enrich themselves, to the detriment of the rest of the company, and to the detriment of the shareholders.

This is not a unique experience, by the way.

Interesting aside: I interviewed well for a senior product manager job at Dell Secure Works, and was given a verbal offer by their VP of Product Management.

But by the time I’d landed in Portland, just a few hours later, he called to report that other members of the executive team had overridden his decision.

And why?

Because when Michael Dell had moved Secure Works directly within his organization, he told them that organic growth was acceptable.

The executive team did not want nor did they welcome inorganic growth.

And again: this is not unique. Mediocrity is the gold standard, enforced by an executive management caste that negotiates their exit compensation prior to their even being hired.

I’ve worked in Fortune 1000 companies, and no small number of other companies in the $30m-$150m range; fear-based inaction and general cowardice and ineptitude on the part of the executive caste is the norm, not the exception.

They love the words “accountability and action” but don’t really know what that actually looks like, because their decisions are driven by self-interest.

Plot twist: this story isn’t about Tripwire.

The company effectively failed; although it was their aspiration to go public, they were acquired by a larger company after the executive caste failed to deliver upon their high aspirations.

And why?

Because they were unable to do much beyond milking their existing customer base of maintenance revenue, meaning that they failed to deliver upon innovation in a timely manner, and believe me: time is an important consideration.

And although it’s common to blame R&D for the failure to deliver upon innovation in a timely manner, it’s also important to acknowledge that within this company, corporate direction would shift 180 degrees about every six months, meaning that the engineering team was bogged down in “technical debt” trying to deliver upon the insane demands of an executive that was incapable of making a decision, and sticking to it.

In common parlance, this means that the engineering team was no longer able to honor the insane number of checks being written from the executive team, because their direction swung wildly every six or so months. So, engineering closed ranks, and it’s hard to fault them.

And, I should note, this same stubbornness on the part of R&D is likely why the Tripwire Log Center is still for sale, and why it has an 93% recommended purchase score.

This is the point of this article:

If there’s no competent leadership from the top, the rank and file tend to step in and fill the gap, right?

(This is where I point out that none of this has to do with for-profit entities: I’m leveraging this example to highlight our problem with the government, using the private sector as an illustrative metaphor).

This story is a small insight into why a majority of publicly-traded companies are not able to service their debt (they are called “zombie corporations”).

(Just as a growing number of governments are becoming more and more insolvent).

The management caste is ordinarily incapable of doing much besides getting in the way, and it’s because they are rewarded, regardless of outcome.

(Same with the politicians and the senior bureaucratic caste, who are compensated many orders of magnitude for their cowardice and incompetency, to the detriment of their “constituents”).

And all along they are praised for their leadership.

(Same in the private and the public sector, no?)

Q: what if we are afforded an opportunity to redefine what it means to be a leader? I’d sure like that.

What circumstances might invite the opportunity for us to step forward and fill a gap which may exist in leadership?

(look around: it’s happening now, everywhere)

The “heroes and leaders” sit out COVID-19 in their second and third homes, or tour the country in their half-million dollar RVs or their sailboats, and cry themselves to sleep each night to the echoes of authentic untruths suggesting they are not much more than lampreys, but rarely the salmon, as the indigenous say.

What circumstances may invite our senior leadership and opportunity to seek and secure redemption, through demonstrative merit, within a “performance plan” that emphasizes transparency and accountability?

Seems to me like the times are ripe for a solution, from the bottom-up, no?



Kent Dahlgren

Product management fix-it guy. World-famous people skills. Extremely small hands. (edit) marketing lady says I’m also supposed to say “CEO of software company”