Most founders want to hire an SDR as soon as they’ve closed a few deals. Alexandra Kane (VP of Revenue at Chalk) says that’s a massive mistake.
In this episode of The Drafting Table, we dive into the tactical truths no one tells you about early-stage sales: how founders should approach cold outbound, when to actually hire an SDR, and why your cold email probably sucks.
Alexandra has led GTM at B2B startups across cybersecurity, infra, and dev tools—and she’s seen firsthand what separates real pipeline from vanity metrics.
We cover:
- The actual milestones you need before hiring an SDR
- Why most founders get messaging completely wrong
- A play-by-play on onboarding and coaching junior reps
- How her team drives pipeline from LinkedIn (yes, even with technical buyers)
- Why cold calling isn’t dead
- And what every SDR should send on their fifth day
If you’re a founder thinking about building your sales org—or wondering why your outbound isn’t working—this one is for you.
Chapters:
0:00 Intro
2:00 What most founders get wrong about sales
4:57 When not to hire an SDR
6:00 Why founder-led sales is non-transferable
7:10 The myth of scaling cold outbound
9:40 Cold calling, LinkedIn, and real data on what works
13:00 Why SDRs need to write better emails (with examples)
16:00 How to onboard and coach SDRs the right way
24:00 Personalization that actually works
29:00 Measuring success beyond meetings booked
34:30 Building an SDR team that scales
46:00 TL;DR: Start simple, test everything, and stay patient
