Why PivotDesk exists

I've hired around 200 people. That means I've been on the other side of the table for well over a thousand interviews, and it gave me a front-row seat to how hiring works from the inside.

Here's what I kept seeing: genuinely strong candidates getting filtered out because their move didn't fit neatly into a keyword search or a 10-second resume/CV scan.

When you post a role, you get 200+ applications. For generalist positions (product, analytics, operations) it's often 2-5x that. You physically cannot spend more than a few seconds on each one. If your background looks unusual on paper — wrong industry, wrong country, no obvious title match — you don't get the interview where you could explain yourself.

The gap wasn't talent or effort. It was a structural mismatch between how good candidates present and how hiring funnels filter.

I built PivotDesk because nobody teaches people how to work around that mismatch, and most advice out there is too surface-level to help.

I'm Jeff McClelland. Canadian originally, studied and lived in the Netherlands, now based in Tallinn, Estonia.

I was early at Skype and Wise (formerly TransferWise) — both from the early days, both during the high-growth phases where teams scaled fast and I was hiring constantly. Analysts, data scientists, PMs, People/HR, you name it.

Then I co-founded Salv, a B2B SaaS company focused on financial crime prevention. Over seven years there, my co-founders and I personally interviewed every single hire — roughly 140 people across engineering, product, sales, marketing, legal, finance, compliance, customer success, and operations.

I also know the candidate side. I've gotten jobs twice in countries where I had no network. It took me 172 applications and 8 months to land my first role in the Netherlands from Canada. Looking back, I could have cut that effort by 75% if I'd known then what PivotDesk teaches now.

I write about the mental models between too-abstract and too-tactical business advice at Jeff's Working Theory. You can also find me on LinkedIn.

Three things kept coming up:

1. Great candidates made avoidable mistakes. Not because they weren't capable, but because nobody had shown them how hiring works from the inside. The candidate side of the process is almost entirely self-taught, and without a way to see behind the curtain, people end up guessing at what works.
2. Harder moves got punished hardest. If your next step was obvious — same role, same industry, one rung up — the standard funnel worked fine. The moment you added a role change, an industry shift, or a geography move, the system stopped working for you entirely.
3. Enterprise sales figured this out years ago. I co-founded a B2B SaaS company, and the parallels between a great outbound sales process and a great job search are hard to miss: targeting, sequencing, tailored messaging, disciplined follow-up, preparation for every conversation. It's a deep, well-studied discipline. The playbooks exist — they just haven't been applied to job searching.

Before writing a line of code, I worked closely with early users to test the method behind PivotDesk: how to choose target companies, identify the right people, write outreach that feels specific, and keep a job search moving when the normal application process is not producing any outcomes.

The core idea came from an article I wrote four years ago. The idea hasn't changed, but the execution is far tighter now. What the pilot taught me:

• An article framework wasn't enough. People needed a sequence: what to do first, what comes next, when to follow up, and how to prepare.
• The tedious parts are where people stall: researching companies, choosing contacts, drafting outreach, and keeping track of next steps.
• The method makes intuitive sense, but turning it into action is harder than it sounds. Hitting send on an email to someone you don't yet know takes real courage.
• Most people are learning this kind of job search for the first time. The product needs to teach, not just store execute.

Every piece of PivotDesk — company prioritisation, contact mapping, outreach workflow, follow-up rhythm, and preparation — came from watching real people try to run a relationship-led search and seeing where they got stuck.

PivotDesk is software plus a structured workflow for running a relationship-led job search. It helps you build a target company universe, choose priority contacts, import contact data from your own external contact-data account, write better outreach, manage follow-ups, and prepare for the conversations that matter.

The product is organised into three packages: Map for building the company and contact map, Momentum for the full outreach and tracking workflow, and Prepared for interview preparation and negotiation workflows (available soon).

PivotDesk is not a recruiting agency, placement service, or done-for-you job search. It gives you the structure and knowledge to run a more deliberate search yourself.

Here's what early users accomplished in practice:

• Built scored target lists of specific companies that have the roles suitable for you
• Sent the first tailored outreach messages to real contacts because they knew the message was strong enough to send
• Generated warm referral introductions from outreach
• Hosted informational conversations and early interviews at target companies

Legal entity: Whimsy OÜ, registered in Estonia. PivotDesk is the first product from Whimsy.

Location: Tallinn, Estonia.

Founder: Jeff McClelland — LinkedIn

Legal documents

If you are unsure whether PivotDesk fits your situation, email [email protected].

The best fit is usually an experienced professional making a move that needs context before it makes sense: a role change, industry shift, geography move, or non-obvious story where cold applications are not working.

PivotDesk is a small, founder-led product. That means the system is being built close to real user behaviour, with fast improvements based on what people actually need in a harder search.

It also means the packages are designed not to depend on guaranteed individual access to me. The goal is to make the method useful inside the product itself: clear targeting, strong outreach, consistent follow-up, and fantastic interview prep.

If a material product dependency changes in a way that prevents you from using what you purchased, PivotDesk will provide a reasonable alternative workflow or refund the affected purchase.