Nat Rubel Staines: People buy from people

By Ricky Robinson

There’s a version of your career you plan, and then there’s what actually happens.

Nat didn’t set out to work in sales. She studied marketing and communications, then drifted into SaaS — social media analytics, video analytics, working with brands trying to understand what people actually care about. It stuck, not because of sales itself, but because of what sat underneath it: storytelling. Understanding what lands, what doesn’t, and why.

So when she came across Shorthand, it didn’t feel like a jump. It felt adjacent. Same problem space, different tool. Nearly six years later, she’s still here. That’s not an accident.

When Nat joined, Shorthand was smaller and there wasn’t a lot of structure in the sales process. No rigid playbook. No fixed way of doing things. Just try it, see what happens. As an experienced sales rep, that worked for her. It meant she could have real conversations instead of running a script, and actually understand what someone was trying to do before jumping to a solution. Several years and multiple variations of BANT and MEDDIC later, that’s more or less still how she works now.

But the part that really tests you isn’t learning how to sell like that. It’s coming back and doing it again after everything’s been interrupted.

During her time at Shorthand, Nat’s had two kids. In most jobs, that’s a big life event. In sales, it’s something else entirely. You don’t just come back to a role, you come back to nothing. No pipeline, no momentum, no rhythm, and a version of yourself that isn’t quite the same as before. There’s a moment where you genuinely don’t know if you can still do it.

You haven’t lost it, but you’re also not the same person. And that turns out to matter in a different way. You get more direct, more focused, less interested in wasting your time or the customer’s. You start prioritising faster, listening better, cutting through things you might have entertained before. It’s not easier, but it’s sharper.

That shows up in how she runs deals. She adapts depending on who she’s working with — a global financial institution, a not-for-profit, a university, a brand team trying to figure out how to stand out. But the starting point doesn’t change. Who are they? What are they trying to do? What actually matters to them? Not just the obvious problems, but the ones sitting underneath that haven’t been articulated yet.

From there, it’s about momentum. Not pushing or forcing decisions, just keeping things moving. Taking work off their plate where you can, pulling in the right people at the right time, and making sure the conversation doesn’t stall. It sounds simple, but it’s not. People can tell when they’re being pushed, and they can definitely tell when they’re being sold something that doesn’t quite fit.

That’s the other part she’s clear on. You can’t fake it. If it’s not right, it’s not right. There are deals she’s lost that still stick with her, not because they were bad losses, but because they were close. Because she could see the potential. But the truth is, not every company is a fit, even if you can technically make it work.

The best customers all have one thing in common. They care about storytelling. It's at the heart of what they’re trying to do. They know they have something to say, and they know they’re not doing it well enough. That’s when Shorthand clicks. It usually starts with something big — an annual report, a proposal, a flagship piece — and then expands from there once people see what’s possible.

Where things go wrong is rarely the pitch. It’s what you didn’t uncover early enough. Internal blockers, CMS limitations, approval chains. These are things that only show up after the deal is done unless you learn to surface them up front. That’s where experience shows. Knowing what to ask, when to dig deeper, and when something feels slightly off.

And right now, there’s another layer to all of this. Every conversation involves AI. Customers want to know what it does, what it automates, how far it goes. But almost immediately, there’s a second question: do I still have control? Can I still shape this? Make it mine?

That tension is real, and it’s where Nat sees the opportunity. Not leaning harder into automation for its own sake, but reinforcing what actually matters: the human side of the work. The story, the voice, the decisions that don’t come from a prompt. Because that’s the part people are starting to feel slipping.

Six years in, across different roles, different countries, and a completely different life than when she started, the fundamentals haven’t really changed. Understand the person you’re working with. Tell the truth. Stay close to the outcome. Keep things moving.

Everything else is noise.