Why empowering sales with the right timing (not more hiring) is the key to sustainable pipeline.
My life’s work is rooted in making sales more effective, more pragmatic, and frankly more enjoyable. I’m obsessed with helping sales reps win. Not by replacing them with automation, and not by overengineering their workflows, but by making sure their energy is applied where it matters most: in conversations worth having.
I believe sales is a craft, and when it’s supported by intentional systems, clean data, and marketing that moves in rhythm with the buyer journey, it becomes both efficient and human. The key? Bringing reps in at the right time. Not too early. Not too late. And definitely not as a knee-jerk reaction when pipeline dries up.
That’s why I get concerned when I see companies rebuilding SDR teams because their outbound email “isn’t working anymore.” It’s almost never a rep issue. It’s a timing issue. It’s a sequencing issue. It’s a system that’s skipping key steps and then blaming the players.
Let’s Talk About the Bases
I use baseball analogies a lot when talking about sales, because a healthy funnel isn’t built on home runs. It’s built on base hits – consistently, over time. Every base has a role, and skipping one disrupts the whole play. (BTW, my least favorite sport is baseball.)
Here’s how we break it down:
- First base: Marketing builds awareness – educational, consultative, non-salesy content that meets buyers where they are.
- Second base: Marketing deepens engagement – inviting consideration with product POVs, comparison content, or solution education.
- Third base: Sales steps in – reaching out to warm, engaged leads with outbound plays like emails and phone calls, offering 1:1 conversation.
- Home run: Qualified meetings are booked and real opportunities move into the pipeline.
But here’s the disconnect:
Teams are bypassing first and second base entirely and expecting outbound email (a third-base play) to carry the full weight of demand generation.
It’s not that outbound is broken. It’s that it’s being misused.
The Missing Middle: Second Base is Under-Operationalized
Let’s zero in on second base – the most overlooked and under-leveraged part of the buyer journey.
Here’s what we’re seeing across the board:
- Executives are publishing thoughtful POV posts on LinkedIn
- Paid channels are running awareness-driven campaigns
- Teams are investing in events, private dinners, and community engagement
And yet, none of it is being pulled into a systematic set of timely, trackable touch points before handing leads off to sales.
That’s a critical miss.
Second base isn’t just content…it’s contextual momentum. It’s where interest becomes intent. And if we skip it, our sales reps are left swinging at cold leads with no context, forced into aggression because they’re chasing quota, not guided by insight.
We treat second base as a core operational layer:
- Is this content being sequenced into nurture streams?
- Are these event attendees being prioritized for warm follow-up?
- Are signal-based triggers firing based on behavior, not guesswork?
- Is the sales team aligned on how and when to activate?
If we’re already investing in thought leadership, events, and paid media, but not using them to drive measurable, sales-ready momentum, we’re not maximizing second base. We’re creating content without giving it a job to do.
Premature Prospecting Is Costing You
Let’s talk numbers. Hiring one SDR doesn’t cost just their salary. By the time you add recruiting, onboarding, enablement, and ramp time, you’re easily pushing $100K+ per rep before they generate any ROI.
Yet most teams we speak to admit they’re building or rebuilding SDR teams before addressing the process gaps in earlier parts of the funnel. Every time we ask:
“Are you making this pivot to SDRs before fixing your awareness and engagement plays?”
The answer is always yes.
This isn’t a resource problem. It’s a sequencing problem.
Lead Gen Still Works When It’s Done Right
Email is still the most efficient and effective third-base sales play when the right groundwork has been laid.
The same goes for LinkedIn DMs, which are gaining traction—but only when they’re used with the same patience and contextual timing. Cold outbound works best when it isn’t truly cold.
We make outbound dials—and yes, connect rates are strong. But here’s the nuance:
We only dial once we’ve identified signals from first and second base. Outreach happens after a prospect has engaged with content or taken a behavior-based action.
That’s when outbound converts. That’s when email works.
Don’t Hire People to Patch Process
We’re huge fans of SDR roles. We believe in their value, their hustle, and their ability to drive meaningful conversations. But we don’t believe in hiring people to solve what is fundamentally a process problem.
This is why we anchor our work in enablement. Not just sales enablement, but full-funnel GTM enablement. Because reps thrive when the system sets them up to succeed. And that only happens when we view automation and sales not as tradeoffs, but as teammates.
As Sam Jacobs says,
“Headcount is the most expensive way to create demand.”
So before you add another rep to the team, ask yourself:
- Are we nurturing leads through first and second base with intention?
- Are we translating our marketing efforts into trackable sales signals?
- Are our reps stepping in when buyers are most ready, not just when pipeline is low?
If the answer is no, fix the system first. Then bring in the humans…at the right time.