Tech Sales with Carter

In this episode, I sit down with Kaylin McNamara, Sr. Director of GTM Operations at Owl Labs, to break down what it really takes to build and scale a sales org from scratch, especially when the market is changing fast.

Kaylin walks through how Owl Labs went from an e-comm led motion to a true sales org during COVID, what she prioritized first (data + process before “playbooks”), how they segmented direct vs channel vs SMB, and the leadership principles that helped her earn trust and keep teams aligned through constant change.

TOPICS WE COVER

• What Kaylin did in the first 60 days to stand up sales from scratch
• Why you can’t build a “playbook” until the data foundation exists
• How Owl Labs split direct sales vs channel to avoid self-competition
• The “Swiss Army knife” seller profile for fast, high-volume cycles
• How they handled SMB (BDRs running full-cycle under 200 employees)
• The hardest part of scaling: change moving faster than documentation
• How to earn promotions without politics: reputation + cross-functional trust
• Kaylin’s leadership rule: lead with the why + set clear expectations
• How to raise concerns without killing morale (bring solutions)

ABOUT THE GUEST
Kaylin McNamara is the Senior Director of GTM Operations at Owl Labs, a Boston-based hardware technology company building video conferencing tools for hybrid work. She joined during the early days of Owl’s growth and helped build and scale the go-to-market motion across direct sales, channel partnerships, and international expansion.

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Owl Labs: https://owllabs.com/

In this episode, I sit down with Michael Conrad, Senior Account Executive at n8n, to break down how enterprise AEs multi-thread deals, pull executive buyers in early, and keep momentum without annoying their champion.

Michael walks through the exact assets he built in his first 30 days to drive pipeline: a “land bigger” talk track to increase ASP, LinkedIn org-charting lists to multi-thread with intent, and a follow-up email framework that keeps customers accountable. We also dig into n8n’s inbound-led motion, what they call warm-bound, and how to handle common objections when you are selling a newer platform.

TOPICS WE COVER

• The 3 assets Michael built in his first 30 days that drove pipeline and closes
• The “land bigger” talk track and how to steer deals away from small pilots and increase ASP
• LinkedIn org-charting and how to identify the right personas and multi-thread with intent
• The exact move after Call 1 to create 2 to 3 new threads without burning your champion
• Why the executive buyer should be your first persona, even in inbound-led motions
• Warm-bound and why it works for accounts that already have context
• The hardest objections, including technical clarity and budget, and how Michael handles them
• Rapid-fire tips for enterprise sellers: be bold in discovery and uncover your champion’s personal win

ABOUT THE GUEST

Michael Conrad is a Senior Account Executive at n8n. He sells into mid-market and enterprise accounts and focuses on executive-level deal process, multi-threading strategy, and follow-up systems that drive larger outcomes.

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about n8n: https://n8n.io/

In this episode, I sit down with Matt Stinson, CRO at Starbridge, to talk about what top performing startups look for when hiring AEs, and how candidates can stand out fast.

Matt breaks down how Starbridge is scaling their sales team, why they care so much about ramp speed, and what signals tell him someone will thrive in an early stage environment. We also get tactical on references, back channel diligence, and the exact questions he asks to find the truth behind a resume.

TOPICS WE COVER

• What “ramp fast” actually means and how hiring managers judge it
• The biggest hiring signals for early stage AEs
• How to use references the right way, including back channel
• The best reference question: “If I call you in 6 months and they failed, why?”
• Red flags like the “lone wolf” rep and why that matters
• How candidates should treat interviews like a sales process

ABOUT THE GUEST
 Matt Stinson is the Chief Revenue Officer at Starbridge. He has sold into and led teams across government and education markets, including K 12 and higher education. At Starbridge, the team is building tools that help sellers identify the right accounts to reach out to, when to reach out, and what messaging to use to generate more pipeline.

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Starbridge: https://starbridge.ai/