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 sales, and why he was drawn to startups over larger, more established companies.

We also get into how Grey landed roles at Sunset and Default, why networking and staying close to people over time mattered more than simply sending cold applications, and what candidates should actually look for when evaluating a startup. Grey breaks down the appeal of joining an early team, the tradeoffs of startup life, and some of the most common reasons startups fail, from founder conflict and poor capital management to losing touch with the customer. He also shares why candidates should backchannel current reps, ask much tougher questions in interviews, and treat the interview process as a two-way vetting process instead of just trying to prove they deserve the job.

TOPICS WE COVER

• Grey’s path from nonprofit work into tech sales and why his career path was anything but linear
• How a major injury and long recovery created a resume gap and changed his perspective on work
• What Grey learned at PitchBook about discovery, product positioning, customer curiosity, and outbound
• Why startup sales appealed to him more than staying at a larger company
• How Sunset first became a prospect and later turned into a career opportunity
• How Grey got his role at Default through networking and relationship-building over time
• Why LinkedIn DMs, networking events, and staying in touch can create real job opportunities
• What to look for when evaluating whether an early-stage startup is actually worth joining
• Common reasons startups fail, including founder disputes, careless spending, and weak customer feedback loops
• Why job seekers should ask harder questions, talk to current reps, and treat interviews like a two-way evaluation

ABOUT THE GUEST

Grey Bradshaw-Mack is on the GTM team at Default, a New York-based startup, and previously worked in sales at Sunset and PitchBook. Before entering tech sales, he worked in the nonprofit world, giving him a nontraditional path into software sales. He's also an investor in Mercor.

LINKS

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

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 country.

We also get into how long, complex deals really move forward, from early discovery and deal mapping to validating value across stakeholders and navigating late-stage redlines, negotiation, and procurement. Zac explains why time is the biggest killer of enterprise deals, why indecision is often just a slower version of no, and how he uses urgency, access, and expectation-setting to keep opportunities from stalling out. He also shares how his approach changed once the mortgage market turned, why he leaned more heavily into top-down selling during tighter market conditions, and what he now looks for when coaching AEs through stuck deals, including multi-threading, influence mapping, and figuring out who actually has decision power inside an account.

TOPICS WE COVER

• What it was like being Polly’s founding AE and helping build a sales process without an established playbook
• How Zac used constant iteration and customer feedback to shape the sales motion over time
• Why resilience and adaptability matter when products, messaging, and objections keep changing
• What the first 30 days of a six-to-twelve-month enterprise deal typically look like
• How Polly handles discovery, deal architecture, validation, demos, negotiation, and closing
• How many stakeholders can get involved in large mortgage tech deals and why that complicates the process
• Why time and indecision kill more deals than pricing or contract negotiations
• How Zac uses expectation-setting and urgency to prevent deals from quietly stalling out
• Why giving prospects an easy out can be more effective than chasing dead opportunities

ABOUT THE GUEST

Zac Basile is the Strategic Account Director at Polly, where he focuses on strategic mortgage lender accounts and also helps lead and coach Account Executives across the organization. He was Polly’s founding AE and has spent the past five years helping build the company’s enterprise sales motion, manage complex deals, and shape go-to-market strategy in a highly relationship-driven market.

LINKS

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

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 also get into Kyle’s current thinking on cold email, including why the classic “pain + value + CTA” structure has gotten easier and easier to ignore, how subject lines should create just enough curiosity or doubt to earn an open, and why his team now often starts with a simple “heartbeat check” email before trying to pitch anything. Kyle shares why phone calls still outperform everything else, how he thinks about call backs after the “send me more info” objection, and the cold call structure his team uses to get prospects talking instead of shutting down.

TOPICS WE COVER

• What third-party outbound is and why companies outsource SDR work instead of building everything in-house
• The three main client buckets Kyle sees, from founder-led startups to large companies with internal SDR teams
• Why consistency in outbound matters and why full-cycle reps often struggle to prospect consistently
• Why the old cold email formula stopped working even for highly valuable products
• Kyle’s philosophy on subject lines and how to create curiosity without being overly deceptive
• The “heartbeat check” email approach and why a simple question can outperform a polished pitch
• What patterns instantly make a cold email feel like obvious spam
• Why phone calls still drive the majority of meetings, even in modern outbound
• How to handle “send me more info” without relying on the prospect to reply
• Kyle’s cold call framework, including the permission-based opener, quick value statement, and question-driven approach

ABOUT THE GUEST

Kyle Weiss is the Head of Sales and Customer Success at Outbound Sales Pro and Parakeet. He helps companies build outbound pipeline through a mix of outsourced sales development, cold email, LinkedIn outreach, and phone-based prospecting. Over the past several years, he has worked with a wide range of clients, from founder-led startups testing go-to-market motion for the first time to larger companies looking to scale outbound faster.

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Parakeet: https://www.parakeet.io/
Learn more about Outbound Sales Pro: http://outboundsalespro.com

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 real or just “smoke and mirrors,” and how relationships compound over time inside one vertical. Frank shares why he rarely has to apply for jobs, what he looks for in his first 90 days at a new company, and how small thoughtful gestures inside an organization can make a huge difference when it comes to getting deals done.

TOPICS WE COVER

• What mortgage and proptech sales cycles actually look like, including deal length, buyer personas, and stakeholder complexity
• How Frank evaluates new sales roles like a VC or private equity investor
• What to ask in interviews to figure out whether a startup really has product-market fit
• The biggest career mistake AEs make: making emotional decisions too quickly
• How downturn selling changes when budgets freeze and ROI becomes the whole pitch
• Why a downturn can actually be the best time for a company to replace technology and take market share
• How strong relationships in one niche can lead to opportunities without ever applying for jobs

ABOUT THE GUEST

Frank Pastirchak is the National Sales Director at Reggora. He has spent the past seven years selling in fintech and proptech, including roles as an Account Executive at Reggora and SimpleNexus (now part of nCino). Frank originally started as a BDR at Reggora and is now returning to the company after several high level sales roles across the space.

LINKS

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

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 obsessing over raw KPIs. Tim explains how he coaches underperforming reps, why leaders should speak last in meetings, how adult learning theory shapes his coaching style, and why aspiring sales leaders should learn the full sales cycle before moving into management.

TOPICS WE COVER

• Why Tim’s real estate background helped him land at AppFolio and better understand customers
• How he managed a massive 2025 by focusing on tailwinds and removing friction
• Why great managers create environments, not just accountability
• How Tim thinks about helping reps “get into the zone” instead of just chasing KPIs
• What AppFolio’s “paddle” culture means and why collaboration matters in sales
• The “ship, shipmate, self” framework for making better team decisions
• Why leaders should talk last and create room for reps to lead
• How Tim coaches underperformers by separating skill gaps from motivation issues
• How adult learning theory applies to sales coaching and skill development
• Why future sales leaders should master the full sales cycle before moving into management

ABOUT THE GUEST

Tim McEuen is the Manager of the Enterprise BDR team at AppFolio. He’s spent about 15 years across tech sales, logistics, and sales leadership, with experience managing both AEs and BDRs. Alongside his work in tech, he also built a real estate business, giving him firsthand insight into the customers and industry AppFolio serves.

LINKS

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

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 how lenders can use technology to reduce friction without removing the human element borrowers still want. We close with Dewayne’s advice for mortgage bankers looking to break into fintech, plus why relationships and long-term industry compounding matter more than ever.

TOPICS WE COVER

• Why mortgage domain expertise gives sellers an advantage in mortgage tech
• What pure tech reps often get wrong when selling to lenders
• Why mortgage has historically been slow to adopt new technology
• How borrower expectations are changing the loan experience
• Why the cost to originate has risen so much over time
• Where AI is actually helping lenders today and where there’s still hype
• How to balance automation with the human side of the mortgage process
• Advice for mortgage bankers trying to break into mortgage tech
• Why relationships compound over a long career in one industry

ABOUT THE GUEST

Dewayne Starling is a Strategic Relationship Manager at nCino, where he works with many of the top independent mortgage banking customers in the industry. He has spent more than 30 years in mortgage, with experience spanning loan origination, wholesale and correspondent lending, and mortgage technology.

LINKS

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

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 talk about why vertical SaaS matters and why some buyers actually pick up the phone, how to cold call without commission breath, and what it takes to sell change to customers who did not ask for it. Angie breaks down how Qualia handles reputation-based objections, why empathy is the fastest path to trust, and how her team is guiding customers through major transitions after acquisitions.

TOPICS WE COVER

• Angie’s pivot from medical device sales to SaaS, and how she designed her career around lifestyle and freedom
• The mountain bike sabbatical and van life chapter that forced a reset and led her to software
• Why vertical SaaS matters, including choosing industries where buyers actually answer calls
• Cold calling fundamentals that still win, including discovery first and never pitching without pain
• Why AI spam is hurting outreach, and how to stand out by selling like a human
• How to sell change when customers are resistant, including handling Qualia reputation objections and leading with empathy

ABOUT THE GUEST

Angie Parkhouse is the Transition Team Sales Leader at Qualia. She previously spent 13 years in medical device sales, then took a career sabbatical to compete as a Sponsored Professional Women’s Enduro mountain bike racer. She later pivoted into SaaS to build a career aligned with her lifestyle, and now leads teams helping customers navigate major software transitions and modernize the closing process.

LINKS

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

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/