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How to use a prospect’s career history to create better outreach
When it comes to effective cold outreach, many salespeople focus purely on company research—digging into funding rounds, hiring trends, or recent news. But what about the person you're reaching out to?
Your prospect’s career trajectory can give you deep insight into their mindset, challenges, and priorities. As Will Allred, Co-founder & CEO of Lavender, explains:
"One of the classics is like, they don't post anything on social media. I bet their LinkedIn profile sits there and it looks like a resume, right? At least it looks like a resume. And so if that's the case, I now have a trajectory of this person's career. I know projects they've worked on in the past. I know what they're familiar with, what they're not familiar with. I know a lot about their mindset coming into the challenges that they might be facing in their current role."
Using career trajectory to build a narrative
A prospect’s job history isn’t just a list of roles—it’s a story. By analysing where they’ve been and where they are now, you can craft messaging that resonates on a personal level.
🔹 Big company → Small startup
Sales leaders coming from a structured, process-driven enterprise into a lean, fast-paced startup will likely be craving more structure. They may also have a tighter budget and fewer internal resources—meaning your solution could help them navigate this transition.
🔹 Frequent job changes
A prospect who moves roles every 1-2 years might be highly ambitious and eager for quick wins. They’ll be looking for tools that drive immediate impact and can help them deliver results fast.
🔹 Industry switch
If someone recently moved from finance to SaaS, they may still be adjusting to a different way of working. Messaging that acknowledges their new challenges can create instant rapport.
Making it work in your outreach
Rather than using this insight as the main hook, it can be a subtle but powerful addition—for example, in a PS at the end of your email.
"A classic example would be, like, if a sales leader was coming from a large org, and they're now moving into a small org. And so, if you think about that—big orgs, more structure, more process, more procedure. So if they're going into a small org, they're probably craving that. And so you can speak to that." — Will Allred
How trumpet helps
At trumpet, we make it easier to tailor outreach at scale. Our Digital Sales Rooms allow sales teams to create personalised, interactive spaces for each prospect—turning insights like these into tailored, engaging experiences that build stronger buyer relationships.
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