In this episode, I sit down with Matt Sterenberg, Senior Director of Customer Success at Modern Campus and a 12+ year EdTech leader with experience across customer success, sales, and customer advocacy, to unpack what customer success teams wish every AE understood. We get into how the higher ed ROI debate is changing buying behavior, why “time saved” isn’t a strong value prop unless you can tie it to outcomes, and what it really takes to build trust that turns customers into long-term champions.

We also break down the churn equation: the metrics that actually matter (implementation, time-to-value, usage, sentiment), the hidden risk of “hostage” customers, and the simple pre-close habits that make CS infinitely easier on day one. We close with Matt’s rapid-fire sales advice on why listening is the real superpower, and how a few well-timed questions can save you months of wasted deal cycles.

TOPICS WE COVER

• Why higher ed is more ROI-driven and how that’s changing buying behavior
• Selling value in higher ed: going beyond “time saved” to “to what end?” outcomes
• What creates customer champions, and the fastest ways to lose advocates
• Early warning signs of churn: implementation, time-to-value, usage, sentiment, and champion risk
• The “hostage customer” problem: high usage, low satisfaction
• What AEs should document before close: key stakeholders + pain + success metrics

ABOUT THE GUEST

Matt Sterenberg is the Senior Director of Customer Success at Modern Campus. He’s spent 12+ years in EdTech across customer success, sales, and customer advocacy, including leadership roles at Parchment and Instructure.

LINKS

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

In this episode, I sit down with Sean Gannon, GTM Strategy Consultant at GTMppl and a longtime EdTech revenue leader who spent 13 years at Parchment (later acquired by Instructure), to break down what it actually takes to build predictable pipeline in EdTech and SaaS. Sean shares why most teams start in the wrong place, how to think about data and intent signals in a finite market, and what “getting your data house in order” really means if you want sustainable growth.

We also dig into the selling side: the most common deal killers reps underestimate, how to avoid getting treated like a vendor, and why the best sellers lead with curiosity and equal business stature. We close with Sean’s simple 90-day GTM priorities for any $5–20M ARR leader trying to scale without adding chaos.

TOPICS WE COVER

• Sean’s background and why he moved into GTM advising
• Lessons from 13 years at Parchment and what it taught him about scaling in EdTech
• The biggest lesson for predictable pipeline: start with data, not opinions
• How intent signals and targeting help you win in a finite market
• The most common deal killer: not listening and selling with “commission breath”
• How to stop being viewed as a vendor and sell as a true partner
• Why buyers are far along before they talk to sales, and what that changes
• The shift from gated content to answer engine visibility in an AI world
• Sean’s 90-day GTM priorities for $5–20M ARR teams: data, speed to lead, experimentation

ABOUT THE GUEST

Sean Gannon is a GTM Strategy Consultant at GTMppl. He helps SaaS and EdTech companies design and execute go-to-market strategies that drive predictable pipeline, increase win rates, and turn customers into advocates. Drawing on 20+ years as a revenue leader, including 13 years at Parchment (later acquired by Instructure), Sean partners with executives and their teams to align marketing, sales, and customer success to build growth that lasts.

LINKS

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

In this episode, I sit down with Zach Larabee, Sr. Manager of the Enterprise Sales Coordinator Team at Toast, to break down what actually happens after an enterprise deal signs, how large brands get rolled out across hundreds (or thousands) of franchise locations, and why implementations stall when expectations aren’t set upfront.

Zach explains why franchisee autonomy is the #1 variable that slows rollouts, what sellers should uncover before closing (tech stack, decision rights, and standardization), and how to create urgency with operators who don’t want to be told what to do. We also get into how he won Toast’s Employee of the Year in 2020 by taking initiative during COVID, documenting the process end-to-end, making downstream teams’ lives easier, and building cross-functional trust.

TOPICS WE COVER

• What Enterprise Sales Coordinators do at Toast (the “hybrid” of onboarding + sales)
• How rollouts work when you’re dealing with corporate and individual franchisees
• The #1 factor that determines rollout speed: franchisee autonomy vs corporate standardization
• Why rollouts get delayed at scale (1,000 locations = 1,000 different conversations)
• The best-case scenario: the “standard package” rollout (100 locations in a month)
• What’s often missing at handoff, and what sellers should ask before closing
• Why identifying the customer’s tech stack early prevents onboarding surprises
• Who really derails rollouts (and why it’s usually franchisees, not finance/IT)
• How to create urgency and excitement so owners don’t “stick their feet in the mud”
• Messaging that makes rollouts smoother: finding the operator’s “why” (money, experience, autonomy)
• Handling competitors who try to undercut pricing, and why corporate alignment matters
• How Zach won Employee of the Year: initiative, process documentation, and helping downstream teams

ABOUT THE GUEST

Zach Larabee is the Senior Manager of the Enterprise Sales Coordinator Team at Toast, where he leads a team that manages large-scale enterprise and mid-market rollouts across franchise brands. He’s been at Toast for 9 years, helped scale the rollout motion from the early days, and won Toast’s Employee of the Year in 2020 for his initiative and cross-functional impact during COVID.

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

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/