The Right Way to Reach Out to Decision-Makers

The best executive opportunities on the best terms are generated before they hit the open market. To do this, you need to get in front of the decision maker.

Naturally, the most effective way to do this is to be referred than to go in cold — being vouched for by someone the decision-maker trusts significantly increases the likelihood of engagement — but the reality is that isn't always possible. You may not have any relevant connections, you may be targeting a new region where you don't have a network, whatever the case may be.

If you can't get a referral, you need to reach out directly.

The key to successful outreach is to reframe your approach from an 'ask' to being a solution. You're not asking for a job.

When you understand the challenges a decision-maker is facing and position yourself as someone who can help solve those challenges, you completely shift the dynamic. They need someone like you.

However, you can only be a solution if you know:

1. Your value proposition;
2. The companies and decision-makers who are likely to be having the exact challenges that you solve and need what you have to offer;
3. How to articulate your value and create alignment.

For the decision-maker, wanting to have a conversation with you should feel like a no-brainer. You are the answer to their problems, not another irrelevant candidate emailing them for some unknown reason.

Here's how to do it.

Be Crystal Clear On Your Value Proposition

The first step in successful outreach is being crystal clear about what you bring to the table. You can't be all things to all people as it just dilutes your message.

At the leadership level, the best way to frame your value proposition is to show that you take a company or function from point X to point Y. This speaks directly to what a company needs: someone who can take them from a challenging position to a better, more successful one. There's no ambiguity. It gives decision-makers a tangible sense of what success looks like, and it’s easier for them to understand the transformation you’re offering.

There's more on defining your value proposition here, but as an example:

"I help early-stage SaaS companies transition from founder-led sales teams to scalable, repeatable sales processes that support significant revenue growth. I’ve taken two SaaS startups from $1M ARR to $20M ARR, both inside two years.

Research, Research, Research

Outreach fails when you contact someone who doesn't need what you have to offer. I get a lot of cold outreach from people thinking I run a private equity firm. I don't, but presumably my details have been tagged that way on a data list somewhere. It doesn't matter how good their offering is because I don't need it. Had they done their research, they would have avoided wasting everyone's time.

The same logic applies here. Firing out generic messages or resumes to hiring leaders and hoping something sticks doesn't work. You may get lucky if you happen to get exactly the right person at exactly the right time, but it's not a winning strategy.

You need to do deep research to figure out the companies and decision-makers who are likely to be facing the challenges you help solve. That doesn't just mean their immediate problems, but also what they are likely to face around the corner, based on your knowledge of that space.

The full strategy for company research is here.

Being highly specific in your targeting will naturally mean your pool of potential contacts is a lot smaller, but they will be significantly more valuable and likely to yield results. Five to ten contacts that could result in meaningful conversations trumps 200 contacts that don't reply.

Messaging That Resonates

Once you've got your list of target contacts and their potential challenges, you need to tie that together into a short, succinct email to send to their work email address. I find email gets a better response because not everyone checks LinkedIn regularly, and there's a lot of noise.

Taking the value proposition above as an example, let's say the company research uncovered the following signals for an early-stage SaaS company:

• Raised Series A with ARR reported to be around $1.2M, showing strong early product-market fit. However, there were no recent press releases, news articles or LinkedIn posts from the founder about recent successes, suggesting they hadn't reached any major milestones.
• Looking on LinkedIn, their current (and first) VP of Sales had previously worked at much larger and more established companies, but had no prior experience scaling sales teams at early-stage startups. This raised a red flag that the VP may not have had the right background for a fast-growing, less structured environment, which could contribute to the unusually high turnover among the sales team. Many of the reps had short tenures, often leaving within a few months.
• Looking at customer reviews on G2, many comments pointed to a great product but slow response times and issues with the onboarding process, suggesting poor sales execution and a lack of effective follow-through.

Key takeaway: Likely struggling with sales leadership as they attempt to scale post their Series A.

So, an outreach message to the founder might look like this:

Subject: VP Sales

James,

I’ve taken two SaaS startups (Cloudtech / Nextwave) from $1M ARR to $20M+ ARR as Sales VP. Given where you're at, you may well be going through the same growing pains we did when moving away from founder-led sales.

Might be worth having a conversation if you have 15 mins this week.

John

This works because:

1. It's short and to the point.
2. Clear value proposition — point X to point Y.
3. It shows you understand their challenge.
4. It's strategically ambiguous: you've given them headline value, but not shown all your cards. "Might be worth..." works well because it gets them to think about it — "Hmm. Probably would be worth a conversation."
5. It offers a specific, short time for a call: '15 mins' is doable in anyone's calendar.

Note: you are not sending your resume at this stage. The goal is to get a conversation, where you can then get a far better idea of their challenges and what their wheelhouse looks like.

The Conversation

The first conversation is about fact-finding and building rapport.

Note: you are not asking for a job, or even if they are hiring. You're also not telling them that you're looking for a job.

That doesn't mean dressing it up as something it isn't, but it means being highly strategic in how you frame your conversation. You want to put subtle feelers out without a direct ask.

Following on with the example above, that might go like this:

"James, good to talk. I work in SaaS so naturally I've been following the progress of [company]. Product looks great, but I noticed a lot of churn in your sales team post your Series A, which sounds like you're potentially having the same challenges we had at Nextwave when moving away from founder-led sales. We just hit $20m ARR and are on track for doubling that next year, but I get more excited about the early-stage. If you're looking to really scale your sales function, maybe there's mutual value in exploring something here."

There's no mention of looking for a job, but it opens the door for the other party to start thinking about it and talking about it without you saying it.

The goal of the conversation is to uncover their pain points and align yourself as a solution. Think like a consultant. Tie their problems back to your experience and track record. Give them recommendations, help them see round corners.

In an ideal scenario, this will culminate in them asking you to continue the conversation. If that happens, schedule the date there and then to avoid email tennis and keep momentum. If they ask for a resume, make sure it is highly tailored to their challenges based on the information you uncovered.

At the very worst, you've made a new contact and they are now aware of the value you bring. This can pay huge dividends later.