If you’re searching for a job right now — especially if you’re switching careers, countries, industries, or trying to explain a background that doesn’t fit neatly into one box — “sell yourself” can sound awful.
It sounds like performance, bragging, or becoming one of those weird LinkedIn theatre people. And when you already feel exposed in the job search, the last thing you want is to come across as fake, desperate, or grifty.
Good selling is something much simpler: understanding people. It means figuring out what they care about, what’s broken, what they’re trying to make happen, and whether you can help.
If you’re good at almost any job, you already do this every day. You just don’t call it sales.
One reason this feels scarier than it is: we compare relationship-first job search against doing absolutely nothing uncomfortable. The cleaner comparison is sending applications into the void, repeatedly copying your CV/resume into forms and waiting for strangers to decode your life. This sounds pretty scary, no?
If you want to feel that difference quickly, try Would You Rather: Job Search Edition. It asks you to choose between the relationship-led move and the default job-search move, so you can evaluate which path is more your style right now.
Selling yourself means understanding the buyer
Sales has a bad reputation because bad sales is terrible: pushy, scripted, self-interested, weird.
Good sales is people helping people solve real problems. That is close to most useful work inside an organisation:
- Customer success helps customers get value.
- Product helps engineers and leadership build something useful.
- Operations helps the organisation run smoothly.
- HR helps people succeed in their roles.
- Finance helps teams make better decisions with limited resources.
Different roles, same underlying motion: understand the people, understand the problem, help them make progress.
That’s all “selling yourself” should mean in a job search. You’re not trying to manipulate anyone; the ‘sales’ work you’re doing is understanding what a small group of people needs, then communicate clearly how you can help. That’s it.
A company does not hire you; a few people do
Instead of trying to impress a venerable institution, you’re building trust with specific humans who have real problems they need solved.
Most people don’t job search with this frame in mind. They apply blind, skim the company website, glance at LinkedIn, and show up to the first interview knowing almost nothing about the humans on the other side of the table.
The blunt version: you probably do not know enough yet. The hiring manager’s worries are still invisible to you. So are the team’s failed attempts, internal language, and version of “good” inside that company, country, function, or culture.
So you guess. And guessing is a terrible strategy. It is especially punishing if you’re a non-obvious candidate: switching careers, moving geographies, coming from a different industry, or have a CV/resume that only makes sense once someone hears the story.
You probably already look risky before anyone hears your explanation. A title mismatch, a country move, a sector change, a seniority jump, or a messy-looking sequence of roles can make sensible hiring managers slow down.
That does not mean they are wrong or unfair. They are trying to avoid an expensive mistake. Each person involved in the decision has a slightly different version of that fear: the hiring manager worries about delivery, the senior leader worries about judgement, the team worries about fit, and HR worries about process.
You cannot reduce the perceived risk of hiring you until you know which risks these people worry about most.
You need to sell yourself, yes. But the useful version is not the fake car-salesman version. It is deep understanding, empathy, clear thinking, and a strategy for showing the right people where you fit.
That creates the job-search problem underneath the job-search problem: you need a way to learn before you are judged.
Informational meetings are how you get that information before the interview.
Informational meetings give you the map before the interview
An informational meeting is a short, low-pressure conversation with someone who understands the world you want to work in. The ask is not, “Can you hire me?” It’s, “Can I learn from you?”
Ideally, you speak with people in the orbit of the role: your future lead, your lead’s lead, or an adjacent leader in the kind of team you’re interested in.
They are close enough to the work to know what matters, without the pressure of an immediate hiring decision. Nobody has to evaluate you for a role today. You don’t have to perform. The conversation can be generous, curious, and useful.
A simple structure for these conversations, after a bit of small talk, is TIARA (pioneered by Steve Dalton in The 2-Hour Job Search):
- Trends: What is changing in your industry, function, company, or market?
- Insights: What do outsiders misunderstand about this kind of work?
- Advice: What would you suggest for someone trying to move into this company, role type, country, or career path?
- Recommendations/resources: What should I read, watch, follow, or study?
- Actions: What should I do next to become a stronger candidate?
This can turn a stranger into something close to a lightweight mentor — in the right type of role, at the right type of company.
Not every conversation becomes that. When it does, it is magical. You learn what they care about, what the real constraints are, and how they talk about their team and company.
Later, if a relevant role appears, you are not walking in blind. You understand the humans.
This works because job search is closer to enterprise sales than you think
A quick sidebar, because this helped me understand the whole thing.
At Salv, the company I co-founded, we sold software to banks. We couldn’t afford amazing salespeople in the early days, so sales was mostly founders, product people, and customer success people filling in.
This is normal in startups: founder-led sales, customer-success-led sales, experts selling to expert buyers. It works because buyers like talking to people who understand their world, don’t BS, and can say, “Given what you’ve told me, here’s where this fits…”
Your job search works the same way. You are the product — sorry, slightly gross phrase, but useful — except not a generic one. One of one, really: a weird and wonderful combination of experiences, strengths, constraints, interests, and timing.
Your job is not to spam your CV/resume to 300 companies and hope someone decodes it. The real work is discovering where you are uniquely valuable, and that takes conversations.
(If you want the fuller version of this idea, I wrote more here: The Enterprise Sales Job Search.)
Start small enough that you actually begin
You don’t have to become brilliant at ‘sales’ on day one.
Start with one thoughtful cold email. Then send another, maybe to someone who feels slightly out of your league. Have one informational meeting. Then have another with a different person in the same broad world, so you get multiple angles on the same problems.
(For a deeper look at how this fits into a broader strategy, check out The Relationship-First Job Search.)
By the time you walk into an actual interview, you know far more than you would have known from the job description: the language, the tensions, the real problems, and the point you actually want to make.
PivotDesk is designed to guide you through these steps one by one. It helps you figure out who to reach out to, draft messages that will land, and keep on top of many reach-outs simultaneously. PivotDesk handles the operational layer so you can focus on the human-to-human part.
Thoughtful outreach is more welcome than you expect
This is the part job seekers underestimate. They think, “Why would that person ever want to talk to me?” or “Won’t I be wasting their time?”
Managers deal with problems all day long. A thoughtful reach-out from someone who has done their homework is a pleasant change of pace. If they’re too busy or not interested, they won’t engage, and that’s fine. You move on to someone more open.
When you eventually get on a call, the dynamic is better than you fear. They get to play mentor, share what they know, and advise someone who is actually listening. Your thank-you note afterwards seals the deal.
Almost nobody does this. For many people you reach out to, you’ll be the first person who has approached them this way. Senior leaders have seen plenty of cold outreach, but most of it is terrible. A good note stands out.
People know it’s hard to reach out cold. It takes guts. Plenty of them think, “I want to meet the person with that kind of nerve — they’re probably interesting.” Then they meet you and find out they were right.
You’re on a whole other level than the last 50 people they interviewed: thoughtful, curious, and courageous. Hiring managers notice that. That’s what successful sales looks like.
Better preparation makes you calmer in interviews
If you host a number of informational meetings and follow up kindly, eventually the day comes when you get the opportunity to interview for a role you really want.
Interviews are a handful of touchpoints, maybe three hours total. Decisions still get made from that small sample.
Nerves matter. Hiring managers want competent, relaxed adults who can handle challenging situations. When you come across as jittery, unprepared, or unconfident, they start wondering whether the role will overwhelm you.
The solution is not affirmations in front of the mirror. It is proper sales techniques that will give you the confidence to shine:
- Preparation gives you substance. You’ve done the research, had the conversations, and thought about what the company actually needs.
- Volume gives you perspective. When you have multiple conversations going and several possible paths forward, any single interaction stops feeling like a life-or-death referendum. Your nervous system calms down.
That combination can transform your interview presence. You speak more plainly, ask better questions, and stop overperforming.
Relationship-first search is awkward at first, then it becomes normal
The first cold email is the hardest. Your first informational meeting is a little awkward. By the third or fourth, you start to wonder what you were so nervous about.
You’re not doing anything weird. This is just reaching out to people, having real conversations, and learning about problems you can help solve.
The version of you that has done this a dozen times walks into interviews with a kind of calm confidence that is impossible to fake — because it isn’t fake. It’s earned.
So go sell yourself. Do it properly, in a way that feels like you.
And if you still feel the old dread when you think about reaching out, spend a few minutes with Would You Rather: Job Search Edition. It puts the scary relationship-led moves next to the default job-search moves people keep choosing by habit. You may find the brave option is cleaner than the passive one.
Then use PivotDesk to make the deliberate path easier to run.
