Promote Within VS External Hire

Ever felt like you were on top of your game because everything you know was self-taught, battle-tested, and proven? That was me. From the ground up, I helped build a company, doing everything from individual contributor to leading the team. All while doing sales operations too. I thought I had the playbook down to a science.

The Double-Edged Sword of Internal Promotion

Don’t get me wrong – I'm all in for the hustle and heart it takes to build something from scratch. That entrepreneurial spirit is the cornerstone of every great story. BUT… sometimes, when you're knee-deep in the trenches, it's hard to see beyond the hill.

Here's the deal: What got you “here” might not get you “there”. And by “there”, I mean beyond the horizon, to places you've only dreamed of.

Jumping ship to different startups and industries, I quickly realized something: what worked in one sandbox didn’t always fly in another. Every new team, challenge, and industry landscape showed me gaps in my seemingly bulletproof knowledge. Here's what I found on the journey:

1. Messaging Misses: Sometimes, we're too close to the product. Our messaging ends up more about what we love than solving our customers' actual pain points. Stepping back, or better yet, getting an outside perspective, can make our value proposition crystal clear and directly aligned with what the market needs.
2. CRM Conundrums: Oh, the CRM – our treasure trove of data that’s often as messy as a teenager's bedroom. Many of us set it up in a rush and never look back. But imagine if it was organized and leveraged properly. I've seen companies turn their CRM from a simple contact list into a powerhouse of efficiency and insights, predicting customer needs before even they know.
3. Sales Process Slip-ups: It's easy to think a charismatic pitch and a firm handshake are enough. Yet, without a structured sales process, we're just throwing darts in the dark. I’ve witnessed firsthand how establishing a clear, repeatable sales methodology can transform erratic success into consistent performance.
4. Outbound Strategy Oversights: If your only strategy is waiting for leads to come to you, you're missing out. Diverse industries taught me the value of a proactive outbound strategy—reaching out, creating connections, and sparking interest before the competition even knows there’s a game to be played.

And here’s the kicker: I thought I knew it all because I'd been there since Day 1. But it’s not just about what you build; it’s about the foundations you don’t even realize are missing.

What options do you have?

One of the biggest things I’ve learned through consulting and working with a private equity group is the ability to help companies see the gaps they don’t know they have. To show them worlds they didn’t know existed and strategies they hadn’t considered. But here’s the thing: being open to change is key. It’s tough to shift gears, especially when you’ve poured everything into getting to where you are.

Bringing It All Together

Yes, reward loyalty and promote from within. That drive and dedication are irreplaceable. But also, be willing to pull in external insights. Be open to examining and revamping your messaging, rethinking your CRM strategy, tightening your sales process, and reevaluating your outbound efforts.

The bottom line: What got you here won’t always get you there. External perspectives can highlight paths and possibilities you never knew existed, ensuring that your growth isn’t just a continuation but an acceleration of your success.

To those who’ve built something from nothing: your journey is incredible. But remember, every now and then, it pays to ask for directions. Here’s to leveraging best practices and opening our eyes to the full spectrum of opportunities.

P.S. Not everyone with experience has the experience you need. Size, stage, type of customer, sales cycle, market... all play factors. I've been there when "THE GUY" was going to take us to the next level. His impact was felt in a very negative way. He tried to push his playbook from his big company into a small and growing company. It failed miserably. Big names don't always have big impacts. You want someone who can understand first and recommend second. The one size, fits all approaches never work.