Shows
Tech Sales with CarterHow to break into tech sales without a perfect background | Grey Bradshaw-Mack (Default)In this episode, I sit down with Grey Bradshaw-Mack, GTM at Default, to talk about his unconventional path into tech sales, from starting out in nonprofit work to breaking into software sales through PitchBook and eventually moving into early-stage startup roles. Grey shares how a major skiing accident forced him to relearn how to walk, created a difficult gap in his resume, and ultimately shaped the way he thinks about resilience, discipline, and telling a compelling story in the job market. He also explains what he learned at PitchBook, why that experience gave him such a strong foundation in...
2026-03-1335 minTech Sales with CarterHow to Win Deals That Take a Year to Close | Zac Basile (Account Director, Polly)In this episode, I sit down with Zac Basile, Strategic Account Director at Polly, to talk about what it’s actually like to sell enterprise mortgage tech when there’s no playbook, deals take six to twelve months, and buying committees can range from a handful of stakeholders to dozens of people across the organization. Zac shares how he went from Polly’s founding AE to a sales leadership role, what it took to help build the company’s sales process from scratch, and how constant iteration shaped the way Polly sells into some of the largest lenders in the coun...
2026-03-1221 minTech Sales with CarterWhy your cold emails suck (and what to send instead) | Kyle Weiss (Parakeet)In this episode, I sit down with Kyle Weiss, Head of Sales and Customer Success at Outbound Sales Pro and Parakeet, to break down what third-party outbound actually is, why some companies outsource it instead of building SDR teams in-house, and what’s still working in outbound right now when everyone’s inbox is flooded with the same tired sales messages. Kyle explains the three main types of companies that hire outside outbound teams, from founder-led startups trying to minimize risk to larger venture-backed companies looking to scale pipeline fast without adding a ton of internal headcount.We a...
2026-03-1237 minTech Sales with CarterPick your next sales role like a VC | Frank Pastirchak (Sales Director, Reggora)In this episode, I sit down with Frank Pastirchak, National Sales Director at Reggora, to break down what selling into mortgage, banking, and real estate actually looks like when deals are long, complex, and heavily relationship-driven. We get into how Frank thinks about timing in volatile markets, what changes when budgets freeze, and why the best reps in proptech don’t just sell well, they evaluate companies and career moves like investors.We also talk about how Frank vets startups before joining them, why he brings trusted customers into the interview process to test whether a product is...
2026-03-0815 minTech Sales with CarterHow to Build a Sales Team That Doesn't Need You | Tim McEuen (AppFolio)In this episode, I sit down with Tim McEuen, Manager of the Enterprise BDR team at AppFolio, to break down what great sales leadership actually looks like in practice. We get into how Tim built structure across a huge year personally and professionally, why he focuses more on removing friction than rigid time blocking, and how that same mindset shows up in the way he leads his team.We also talk about the kind of culture Tim believes creates great sales organizations: one built around collaboration, shared success, and helping reps get into the zone rather than...
2026-03-0619 minTech Sales with CarterHow to Sell Tech to an Industry That Hates Change | Dewayne Starling (nCino)In this episode, I sit down with Dewayne Starling, Strategic Relationship Manager at nCino and a 30+ year mortgage industry veteran, to talk about what actually matters when selling technology into mortgage. We get into why mortgage domain knowledge still gives sellers a major edge, what pure tech reps often get wrong when they try to sell to lenders, and why mortgage remains one of the hardest industries to change.We also break down where AI is actually creating value in lending versus where there’s still hype, why the cost to originate has risen so sharply, and ho...
2026-03-0615 minTech Sales with CarterFrom Pro Mountain Biker to B2B SaaS: How to Design Your Career Around Your Life | Angie Parkhouse (Qualia)In this episode, I sit down with Angie Parkhouse, Sales Leader at Qualia (real estate transaction management software), to talk about what it looks like to design your career around your life and the sales fundamentals that still matter in a world drowning in AI spam. Angie shares her unconventional path from B2B sales and 13 years in medical devices to taking a sabbatical to race mountain bikes, living the van life adventure, and ultimately pivoting into SaaS so she could build a career that supported the lifestyle she wanted.We also get tactical on selling. We...
2026-02-2721 minTech Sales with CarterCustomer Success Secrets Every AE Needs to Know | Matt Sterenberg (Modern Campus)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-t...
2026-02-2321 minTech Sales with Carter25 years of EdTech sales lessons and an $835M exit | Sean Gannon, GTMpplIn 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 avoi...
2026-02-1926 minTech Sales with CarterHow to Run a 4,500-Location Enterprise Rollout (In One Year) | Zach Larabee (Sr. Manager at Toast)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...
2026-02-1825 minTech Sales with CarterBuilding a Sales Org From Scratch During COVID | Kaylin McNamara (Sr. Director, GTM at Owl Labs)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
2026-02-1129 minTech Sales with CarterHow to Turn Inbound Leads into Enterprise Deals | Michael Conrad (Enterprise AE at n8n)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 newe...
2026-02-1009 minTech Sales with CarterHow to Get Hired as an AE at a VC-backed Startup | Matt Stinson (CRO at Starbridge)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 COVERWhat “ramp fast” actually means and how hiri...
2026-02-0320 min
Book Reviews for Average PeopleLife Advice From Death RowThis is the quick and dirty review of the book "Life Advice From Death Row" by Carter Armendarez.
2024-01-1505 min
The Winning Youth Coaching Podcast: Youth Sports | Coaching | Parenting | Family ResourcesWYC 145 – College Recruitment – Carter Armendarez talks college recruitment do’s and don’tsCarter Armendarez is a senior at Wesleyan University, where he's also captain of the wrestling team. Getting recruited to play sports in college is confusing to lots of athletes, but it really shouldn’t be. Carter has seen too many athletes fail to get recruited. So he made Acute Recruit’s College Recruitment Guide for Athletes so that doesn’t happen anymore.
Website: acuterecruit.com
Facebook: /Acute-Recruit-369368080173002/
Listen Now:
Listen on iTunes: iTunes link
Listen on Stitcher: Stitcher link
Listen on Google Play Music: Google Play link-
-
The best coaches...
Believed in me
Had me focus on becoming an expert in o...
2018-03-2200 min
The Winning Youth Coaching PodcastWYC 145 – College Recruitment – Carter Armendarez - College recruitment do's and don'tsWYC 145 – College Recruitment – Carter Armendarez - College recruitment do's and don'ts Carter Armendarez is a senior at Wesleyan University, where he's also captain of the wrestling team. Getting recruited to play sports in college is confusing to lots of athletes, but it really shouldn’t be. Carter has seen too many athletes fail to get recruited. So he made Acute Recruit’s College Recruitment Guide for Athletes so that doesn’t happen anymore.
2018-03-2234 min