Anyone who has tried to book time with a CEO knows how it goes. You research the company, customize your outreach then follow up a couple times. Eventually you land in an assistant’s inbox and maybe you get a polite reply, but more often than not, you’re met with radio silence.
It isn’t that senior executives are unreachable. It’s that with everyone vying for their limited attention, the usual routes to them were built to keep people out.
Why the top of the org chart matters
Big partnerships rarely rest on one enthusiastic champion. Gartner’s research on complex purchases points to buying groups of six to 10 people, with vendors getting only a sliver of their time. But the people at the top still set the terms: what’s a priority this year, what gets budget and which risks are worth taking.
Get in front of them early and something shifts. You stop guessing at what keeps a CEO up at night because you’ve heard it directly. A leader who knows your name and trusts your judgment also tends to ease the path for everyone below, from procurement to legal. That’s how deals close faster and on better terms, with partners who are treated as more than a vendor.
Why it’s so hard to get there
Cold outreach works often enough that people keep doing it, but not by much. Average meeting-booking rates sit around 2 – 3%. At the executive level the obstacles stack up.
Assistants and switchboards guard the calendar. Schedules fill months ahead. Your email competes with hundreds of others. Requests get quietly handed to someone who can express interest but can’t say yes.
Without a mutual contact or existing relationship, even a sharp pitch looks like everything else in the inbox. Sometimes even the timing is simply off, because senior leaders tend to focus on whatever problem is in front of them that week.
None of this is a failure of effort. It’s structural, and working harder at the same channels rarely fixes it.
The other way in
One alternative is to go where executives are already talking about the things they care about. At OBJ, we do a version of this four times a year through our Executive Report series.
Each report starts with a private roundtable of eight to 12 hand-selected c-suite executives from a single sector. We moderate the discussion on trends, challenges and opportunities, and our writers use it as the foundation for the report.
While partner companies also get a profile in front of a highly targeted readership, the most valuable perk for business development is the exclusive invite to the roundtable luncheon. Advertisers get to sit in on the conversation and connect directly with the executives all in one space. Reading about a sector’s priorities after the fact is one thing. Hearing leaders talk candidly about which projects are moving, what’s stalled and where they could use help is another.
Now to be clear, this is not a substitute for relationship-building, and a seat at the table won’t close a deal on its own. But it does shorten the distance to a first real conversation with the people hardest to reach, and that’s an opportunity you can’t get just anywhere.
Making the most of your seat
A few habits separate the companies that get something out of these rooms from those that don’t.
- Send someone senior enough to speak as a peer, and brief them beforehand on who will be there.
- Resist the urge to pitch. The best conversations at these events usually start with a question.
- Listen for the language leaders use to describe their problems, and write it down.
- Then follow up within a week, refer to something specific you heard and offer an idea or an introduction before asking for a meeting.
The profile deserves the same care. A thoughtful piece on a real challenge in the sector will do more for your reputation than any standard piece of content, and the executives who read it will remember who said something useful.
Finally, be patient. Some of these relationships pay off months later, when a pain point mentioned at the table turns into a funded project.
What’s next
If you’d like to know which sectors OBJ’s Executive Reports will cover next, reach out to sales@obj.ca.
We’re also now looking for partners for our Executive Report on Tourism + Hospitality, set for February 2027. Contact us before October 14 to secure your invite.
Author Bio
Eric Dupuis is a senior account executive with Ottawa Business Journal. OBJ’s content team handles hundreds of local and regional B2B campaigns every year across print, digital and event platforms. To audit your current media mix or explore integrated campaign options, connect with Eric directly at eric@obj.ca.
