Session Notes

Go-To-Market

Outbound is Dead. Long Live Outbound.

Haley Brannan

If you find yourself with more questions than answers about outbound demand gen, you're not alone. The tools, the hires (is the entry-level SDR a thing of the past?), the metrics - everything feels up for debate right now. There's no shortage of hot takes, but what we've heard would be most useful to founders is hearing from other founders whose outbound strategy is actually working at the early stage.

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And that's exactly what our latest CEO Confidential session delivered. We brought together two OpCo portfolio CEOs who've recently rethought their entire approach to outbound, leveraging automation and AI at every step. Dylan Ratcliffe, Founder/CEO of Overmind and Alex Calder, Co-Founder/CEO of Coworker, shared the specific approaches they’ve taken for outbound demand gen. The best part - they have two totally different approaches!

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The conversation tackled what's still relevant from traditional SDR playbooks (and what's not), how to use AI without sounding like a bot, the economics of in-house teams, and the specific techniques that actually get prospects to respond. We were also very fortunate to have Operator LP and OpCo Board of Advisors member Erica Ruliffson Schultz, former President of Field Ops at Confluent, join us for an AMA on how to approach scaling revenue orgs today. The session was held under Chatham House rules, so no attributions - just candid, tactical takeaways from founders in the trenches.

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Here are the session notes:

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The LinkedIn Play: When Personal Touch Actually Scales

One founder shared their bottom-up approach targeting specific technical buyers at companies writing six-figure deals.They went all-in on LinkedIn after email outbound failed completely for their ICP.

The process is deliberately human at key points. Start with broad LinkedIn filtering, scrape profiles with a data-driven prospecting tool, then use AI via Zapier to filter out contractors and non-ICP leads. The AI is shockingly good at what LinkedIn's native filters miss.
Connection requests are personalized, not templated. The system generates drafts based on actual skills and profile content, but humans approve every message using their real LinkedIn profiles. Your own reputation is on the line so you need to stand behind the message.
Results speak for themselves: 30% connection rate, 3-4% conversion to actual calls. That's 3-4 qualified calls per week per person running the process. From an LTV/CAC perspective, this works out to very positive economics.
Team structure is lean: Founder + product person + 1 BDR executing the entire operation.
AI prevents wishful thinking. They built a SPICED qualification framework where the system won't advance deals without required information. In other words, the sales team (including the founder!) does not have the authority to move a deal to the next stage in the pipeline - you have to convince the AI that it deserves to be pushed forward. No more "this feels like it's going to close" without actual data to back it up.

The key insight: email didn't work for this technical audience, but a thoughtful LinkedIn approach that respects their time and speaks their language does.

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The Email Play: When Volume Is the Strategy

On the opposite end of the spectrum, another founder runs what can only be described as industrial-scale cold email. We're talking 1,900 inboxes sending over a million emails per month by 2026 (currently at 80,000 weekly).

Infrastructure is everything:

Multiple domain variations because you run out of domains fast
Email warm-up services for every inbox
Email rotation to keep volume per inbox low and avoid blacklisting
Lead verification and list cleaning to prevent inbox death

The economics work:

$105 cost per call booked
Best reply rate: 2.8%
Best conversion rate: 0.35%
Minimum 30x ROI on 30k+ ACV deals
Monthly investment: roughly $20k

What actually drives success:

Volume, not manual personalization. This isn't about crafting 50 perfect emails. It's about sending thousands.
Speed. A human responds to every reply in 5-10 minutes using an offshore team for coverage. The spike in conversion from fast response is dramatic.
Human-written copy with minimal AI. One really short, specific personalized line via Clay, then the rest is punchy human-written value props. The long-winded AI personalization is obvious and doesn't work.
A full-time "go-to-market engineer" managing the entire operation. Not a marketer, not a traditional SDR - someone technical who can write code to make all these tools work together.

The hot take that surprised everyone? Nobody remembers if you've emailed them before unless you were spammy. So the most successful approach is sending multiple emails from different domains to the same people every few weeks. Not follow-ups. Net new emails.

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Enterprise Sales Wisdom: What Actually Changes at Scale

Erica brought hard-won lessons from scaling to over $1B in revenue and going through multiple business model transformations.

Work customer-back, always:

Start with ICP (the company profile, not just the person)
Define buyer personas within those companies
Design your engagement model based on how those people actually want to buy

The SDR/BDR role evolved dramatically at Confluent:

Traditional SDRs still worked for CTO-level outreach (think executive dinners and high-touch content)
But for technical buyers who started in the PLG flow, they created "Technical Customer Success Representatives" - people who didn't aspire to be in sales, wanted to be SEs, and focused on getting users successful rather than creating pipeline
The ratios flipped from conventional wisdom: multiple technical resources per AE for complex products, not the other way around

Multi-threading is non-negotiable:

Parallel outreach to different personas within the same company
Technical profiles engage engineers with technical content
Traditional AEs target executives with business value conversations
Don't wait for one thread to develop before starting another

Modern AE requirements have changed:

Must be technically fluent enough to not immediately defer to SEs
Earlier-career hires are attractive because they don't have legacy bias
Sales engineers can make excellent AEs (though some prefer to help rather than drive, so hire carefully)

Organizational Design: There's No Perfect Answer

The group discussed first hires and reporting structures with refreshing honesty about what actually matters.

SDR/BDR reporting is flexible:

Sitting within the Sales org preferred for career development and mentorship
Within the Marketing org acceptable if you have a really strong demand gen leader
The right answer depends on your leadership strength, not some universal best practice (and remains and will always remain a topic of debate within orgs)

First hire considerations:

GTM engineer vs traditional SDR depends entirely on your strategy
If you want cold calling, that requires a very specific personality type
If your strategy is unclear, hire a smart generalist who can figure it out
For technical products, you need technical profiles throughout GTM

ICP definition framework:

Industry + company size + "what has to be true"
Example: Not all financial services companies, but tech-forward companies within financial services (think Capital One before Wells Fargo)
Top 1000 prospect lists are valuable even when you can hit volume at scale

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Technology and Automation: No Magic Bullet Exists

Everyone asked about AI SDRs. The answer was unanimous: nothing good exists yet as an out-of-the-box solution.

What you need instead:

Custom code. One founder showed six different tools working together. The other's setup was even more complex.
Multiple tools integration is mandatory
Human oversight at critical points to build trust

Where AI actually excels:

Lead filtering (contractor detection, profile matching based on skills)
Message generation when you provide strong frameworks
Deal qualification enforcement (preventing wishful thinking)

Essential pre-work:

Clear ICP definition - and clarity amongst the whole team on what this is - before you pick tools or hire anyone
Without this, you're just throwing money at vendors

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Key Tactical Takeaways

The session wrapped with rapid-fire insights that cut through the noise: