What 10+ Years in Proposals Teaches You (That Most Organizations Still Miss)

A bid manager's view from inside the churn: credibility, chaos, AI, and why proximity to real work still matters.

By Timmy Semenza, Boss Key LLC | Published February 25, 2026

I have worked on proposals for more than ten years, and I am not here for nostalgia about the good old days. Remember PMAPS? Lotus Notes?

What I keep coming back to is the feeling of credibility you know you have, and how easily it gets squashed by the organization around you. Bid managers have a line through the organization that few other people can lay claim to. You have to make the rounds inside the company on a comprehensive basis just to do your job.

The irony is that lots of people will know your name and interact with you, and they may even find you to be great to work with. Fundamentally they probably will not know what you are actually creating while you are there.

To be a bid manager is to be a repository for organizational chaos. You exert a calming influence to the extent that people just like having you nearby to absorb the uncertainty attached to business development. That is a strength that is hard to come by elsewhere in most organizations.

The Orchestrator Problem

I am reminded of what Steve Jobs said in the film of the same name, when he was asked what he actually does for the organization since he does not seem to have anything tangible to show for it. He responds that he plays the orchestra.

Proposal managers are obviously operating on a different scale from the co-founder of Apple. The parallel is still real: a bid manager needs to understand the inner workings and operations of the company while also keeping enough academic remove to synthesize it into something coherent.

Bid management is both operational fluency and editorial distance, at the same time.

My Uncomfortable Admission

I have spent the last five or so years in the janitorial industry and I am ashamed to say that my hands are as soft and uncalloused as they have ever been. I do not know what it is like to get lower back strain from pushing a Kaivac around all day. I have only ever written and talked about it.

My main regret is that I have not been able to get out into the world enough to truly understand what it means to be behind one of those machines. I do not want to be patronizing or paternalistic toward people who perform janitorial labor. But the fact is that I have made my living off the hard work, effort, sweat, and struggle of people doing work I would never myself want to do, and I have spent a lot of time writing about it as if I knew the first thing about it.

Why This Matters More in the AI Era

I would love to see bid managers get the opportunity to get out into the world and truly understand what it is like to do the work they write about. I want to be in the trenches with the people executing the work I have been writing about.

I am reminded of Alex Garland's Civil War, with Kirsten Dunst, Cailee Spaeny, and Wagner Moura, and the way those photojournalists are on the front lines trying to report accurately without sensationalizing things, at great personal cost.

Bid managers should never have to be under direct fire to do our jobs. There is still a real lesson there about the value of frontline positioning. With the temptation to use AI to write the proposals we are being asked to churn out at greater volume every day, the only way to differentiate as a selling organization is to have someone who can directly convey and translate the experience of the work itself into the minds of evaluators.

I love AI and automation. The real differentiator is still the squishy human being who has seen the work up close.

To paraphrase a line about the futility of film criticism, using AI to write about service delivery is like dancing about architecture. You cannot pierce the veil if you do not understand what you are writing about, and that means getting out into the world and experiencing it with your senses.

What Organizations Should Do Next

I believe organizations that employ bid managers owe it to them to get them into the field as much as possible, in the passenger seat alongside the people delivering the work, whether that is janitorial operations, a CI/CD pipeline, or claims response operations.

• Put bid managers on client visits.
• Put them on site visits.
• Put them on intake calls with the sales team.
• Put them in co-solutioning sessions early in the process.
• Use remote-first for mobility and field access.

The main advantage of bid management being remote-first is flexibility and mobility. We can be deployed wherever we need to be to get to the heart of the work we are writing about.

Final Thought

Everyone is talking about AI because it gets clicks. The real secret weapon is actual human beings who can get out into the world, observe, judge, and come up with ideas. Bid managers do more than write what a company does. At our best, we help a company understand what it is.

If this resonates with how your team is thinking about growth, capture, or proposal quality, I would welcome the conversation. This is the work I care most about, and the work I do with Boss Key.