In the Loop with Holly & Angi

About In the Loop with Holly & Angi

In the Loop with Angi Milano and Holly Glowaty. The GTM Loop podcast is where founders, operators, and industry leaders get real about building go-to-market strategies that actually work. Each episode breaks down the moves that drive growth, from selling to banks without losing your mind to turning compliance into a sales advantage. Expect candid conversations, practical tactics, and stories from the trenches that help you sell it, keep it, and grow it.

Publisher

Angi Milano & Holly Glowaty

Category

business · technology

Language

en

Explicit

No

First episode

8 Oct 2025

Latest episode

29 Sept 2026

Latest episodes

15 episodes in the feed.

1. 

   29 Sept 2026

   Ep 15: Your Badge Scan Is Not Pipeline

   Conference season is here, and so is the questionable pipeline math. In this episode, Angi and Holly talk about what it really takes to get value from fintech conferences before, during, and after the event. They get into the difference between a good conversation and a real opportunity, why badge scans should not automatically become pipeline, and how to decide which follow-ups deserve your time once everyone gets home. They also cover conference planning, where to spend your time and budget, what to measure, and how to think about ROI beyond the number of names sitting in your CRM. Because conferences can absolutely create relationships, opportunities, and revenue. But a packed calendar and a stack of badge scans do not tell you whether the event worked. Expect straight talk, practical advice, and the occasional hair flip. Sell it. Keep it. Grow it.

2. 

   24 Aug 2026

   Ep 14 - The Bake Sale Is Not the Strategy

   What do declining nonprofit membership, the loneliness epidemic, walking groups, and startup methodology have in common? More than you might think. This week, we are joined by Deborah Hill, Founder & CEO of Seahorse Innovation Lab, to talk about what happens when you take lessons from 30+ years in technology, finance, and startups and apply them to building community. Deborah is helping membership organizations rethink how they attract and engage new members by starting small, running experiments, listening to feedback, and measuring whether people are coming back. And it turns out, the lessons apply just as well to startups. The conversation gets into why a simple experiment can teach you more than an elaborate plan, the difference between activity and real traction, why retention tells you more than attendance, and what you can learn from the people who stop showing up. They also talk about building communities people genuinely want to be part of and creating opportunities for members to become the next generation of leaders. Because whether you are building a startup, a nonprofit, or a walking group, doing more does not necessarily mean you are building something people want to come back to. Connect with Deborah Hill: LinkedIn: https://www.linkedin.com/in/deborahhill Seahorse Innovation Lab: https://seahorseinnovation.com (https://seahorseinnovation.com) The Lean Startup: https://theleanstartup.com/book Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll want to listen to. Sell it. Keep it. Grow it.

3. 

   27 Jul 2026

   Ep 13 - Hiring for Impact

   Hiring can accelerate growth or slow it down. In this episode, we sit down with Sarah Greenwell, Founder of Growth Mode Partners, to talk about one of the biggest challenges founders face: knowing who to hire, when to hire, and what role will make the biggest impact. We explore why founders often hire too early or too late, why your first sales hire may not actually be a salesperson, and why the best hiring decisions start with defining the impact you want someone to make instead of writing a job description. Sarah also shares practical advice on transitioning from founder-led sales, evaluating candidates from larger companies, building teams with diverse perspectives, and using AI to strengthen hiring without replacing human judgment. Whether you're making your first hire or building out your leadership team, this conversation will help you make smarter hiring decisions that support long-term growth. Connect with Sarah Greenwell LinkedIn:  linkedin.com/in/sarahcgreenwell Growth Mode Partners: growthmode.partners Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll want to listen to. Sell it. Keep it. Grow it.

4. 

   12 May 2026

   Ep 12 - You're Leaving 25% of Your Market Behind

   What happens when your product or website isn't accessible? You lose customers. Emily Goodson joins us to break down why accessibility should be built in from day one, not added after the fact. We talk about real-world consequences, from failed user experiences to compliance issues, and how small changes can make a meaningful impact If you are building in fintech or any regulated space, this is a conversation worth paying attention to. Looking to work with Emily? LinkedIn: https://www.linkedin.com/in/ecgoodson/ (https://www.linkedin.com/in/ecgoodson/) Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll want to listen to. Sell it. Keep it. Grow it.

5. 

   27 Apr 2026

   Ep 11 - There's Data… and Then There Are Vibes

   In this episode of In the Loop with Holly & Angi, we sit down with Hanane Bouchareb, Head of Product Management at M1 to talk about the real role product plays in go-to-market strategy. We get into the balance between data and instinct, and why "vibes" actually matter more than people like to admit. When product, marketing, and sales are aligned, it is not just about what gets built. It is about how clearly the team can communicate what matters and why. We also get real about what happens behind the scenes. Features shift, priorities change, and not everything goes according to plan. The teams that win are the ones that stay close to the customer problem and keep everyone aligned as things evolve. If you're interested in learning more about M1, check them out at: m1.com Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll want to listen to. Sell it. Keep it. Grow it.

6. 

   5 Apr 2026

   Ep 10 - Solving the Unnamed Problem

   How process, communication, and decision-making quietly break down as teams scale. In this episode, we sit down with Chrystal Price, founder of In Good Company Co., to talk about something every growing company feels but rarely defines. We see this in repeated meetings that go nowhere, decisions that never stick, and processes that live in people's heads instead of anywhere others can follow. It often gets labeled as a communication issue, but it runs deeper than that. We get into how breakdowns in process, decision-making, and culture start to surface as teams grow, and why they are so hard to fix once they are embedded. Chrystal shares how to spot the early signals, what is really causing the friction, and how to start untangling it in a way that sticks. If you've ever felt like your team is busy but not moving forward, this one will hit close to home. Looking to work with Chrystal? Website: https://ingoodcompanycompany.com LinkedIn: https://www.linkedin.com/in/chrystalcadenprice/ Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll want to listen to. Sell it. Keep it. Grow it.

7. 

   22 Mar 2026

   Ep 9 - Will You Swipe Left on Your Bank?

   Our guest this week is Fabiola Salazar, VP of Technology Banking at Wells Fargo. Fabiola works directly with founders to help them solve one of the most overlooked parts of building a company: choosing the right banking partner. In this episode, we talk about what fintech founders should expect from their bank, why the relationship matters far more than just opening an account, and how the right banking partner can save a founder time, money, and a lot of future headaches. Fabiola also shares what to look for in year one, how banks can support growth beyond deposits, and the questions every founder should ask before choosing a banking partner. Interested in speaking with Fabiola? Reach out via LinkedIn: https://www.linkedin.com/in/fabiola-salazar/ Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll want to listen to. Sell it. Keep it. Grow it.

8. 

   8 Mar 2026

   Ep 8 - Don't Be Clever at the Expense of Clarity

   In this episode of The GTM Loop, we sit down with Arden Evenson of Firefly Advising to talk about messaging, clarity, and why so many companies make their products harder to understand than they need to be. Arden shares lessons from her early days at SoFi, why clarity always beats clever copy, and how founders can improve their messaging by focusing on outcomes instead of features. The conversation also touches on AI-generated content, financial inclusion, and why the best messaging often comes directly from the words customers use themselves. Interested in working with Arden? Here's how: https://evensons.notion.site/The-Messaging-Performance-Audit-30a68749a65281cc92aae7c40dec0a45 Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll actually want to listen to. Sell it. Keep it. Grow it.

9. 

   15 Feb 2026

   Ep 7 - The Pitch Slap Recovery Plan

   In this episode, Angi and Holly talk about what empathetic selling looks like in fintech and why chasing an ICP just because "they have budget" is not a real strategy. They unpack what buyers inside financial institutions are worried about, the personal and reputational risk behind every decision, and why the best sellers spend more time listening than pitching. The conversation covers partnership versus vendor mindset, social selling without the pitch slap, and how empathy shows up not just in sales calls, but in hiring, onboarding, and long-term relationships. If you sell into banks or credit unions, this episode is a reminder that you are always selling to a person first, not just an institution or a budget line. Find the Supercommunicators book here: https://bookshop.org/a/121030/9780593243923 Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll want to listen to. Sell it. Keep it. Grow it.

10. 

    1 Feb 2026

    Ep 6 - Your AI Is Only as Smart as Your Mess

    In this episode, Angi and Holly sit down with Neal Mann, co-founder of Noan, to talk about the part of AI most companies keep avoiding: their foundation. Neal explains why layering AI on top of broken systems does not work, why documents were never meant to be the backbone of modern businesses, and why facts should be the true system of record. Together, they unpack how clean, connected data changes marketing, sales alignment, compliance, content, and customer trust. They also explore human-in-the-loop AI, single sources of truth, financial institution realities, and what founders should prioritize if they want to scale without creating more complexity. This episode is a reminder that AI does not fix chaos; it exposes it. Learn more about Noan here: getnoan.link/thegtmloop Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll actually want to listen to. Sell it. Keep it. Grow it.

11. 

    18 Jan 2026

    Ep 5 – SKO or Expensive Field Trip?

    Sales Kickoff season is here, and Angi and Holly have thoughts. In this episode, they break down what actually makes an SKO useful and what turns it into a glorified team vacation with better lighting. From comp plans and pipeline math to role-playing trauma, ICP clarity, and why trust matters more than touch counts, this one is packed with honest takes and real operator advice. They cover how to equip sales teams with tools instead of pep talks, why role-playing belongs in theater not SKOs, how pipeline math gets misunderstood, and what leaders can do to build trust instead of micromanagement. If your SKO doesn't change how your team sells, it wasn't an SKO. It was just a meeting with snacks. Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll actually want to listen to. Sell it. Keep it. Grow it.

12. 

    29 Dec 2025

    Ep 4 – The Year-End Reality Check

    Let's take a candid look back at what actually changed in GTM over the past year and what didn't. We talk through the real shifts we saw in 2025, including the return of in-person events, the growing focus on credit unions, how rising conference costs are changing how teams show up, and why curated conversations are replacing big booths and big budgets. We also dig into how search, AI, and social selling are reshaping visibility, why tighter ICPs matter more than ever, and what teams need to stop doing as they plan for the year ahead. From pipeline discipline and content creation to practical adoption of AI and voice tools, this is an honest year-end conversation grounded in what we're seeing work in the field. No predictions for the sake of predictions. Just a reality check before you head into planning mode. Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll actually want to listen to. Sell it. Keep it. Grow it.

13. 

    10 Dec 2025

    Ep 3 - Stack It Like You Mean It

    In this episode, we get tactical. We walk through the tools we rely on every day to run our GTM motion, from CRMs to automation hacks. We talk about why spreadsheets are not a sales process, how to pick the right CRM for your team size, and the integrations that actually make your life easier. We share the platforms we use for automation, AI, and content creation, and how they fit together to save time and money. From HubSpot and Streak to Zapier, Clay, and Canva, we cover the tech stack that helps us work smarter. We also talk about the underrated tools like Plaud Note for transcription, CalendarBridge for juggling multiple calendars, and even Rent the Runway for event prep. This one is packed with practical tips, a few laughs, and serious time savers. Core Platforms HubSpot: All-in-one CRM for sales and marketing alignment Streak: Lightweight CRM inside Gmail for consultants and small teams Salesforce: Best for enterprise but often too heavy for startups Zoho CRM and Adio: Affordable options for small teams Automation and Integration Zapier: Automate repeat tasks and connect data between tools Clay: Build lists, identify lookalikes, and enrich data for outreach Vector and Ocean.io: Power lookalike audience building and ICP validation Content and AI ChatGPT, Claude, Copilot: Writing, brainstorming, and automation Canva with CSV integration: Auto-generate branded social posts from transcripts Plaud Note: Hardware and software combo for recording, transcribing, and summarizing ideas Productivity and Operations CalendarBridge: Sync and share multiple calendars across clients Calendly: Simplify scheduling and embed availability in emails Google Workspace: Use built-in tools securely with FI-friendly settings Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll actually want to listen to. Sell it. Keep it. Grow it.

14. 

    12 Nov 2025

    Ep 2 - Create Demand, Don't Chase It

    Angi and Holly get real about early pipeline. We cover how to define an ICP, why you need at least three buyer personas, and what it takes to reach a cold contact. Hint: plan for 8 to 12 touchpoints. We unpack channel preferences, why text can beat cold calls, and how to warm specific accounts with domain-targeted LinkedIn ads. Most of all, we show how sales and marketing share signals so messaging evolves, campaigns have time to work, and progress is measured by engagement and learning, not just demos. We explain how to define your ICP and core personas, plan meaningful touchpoints, and mix text, email, events, and targeted ads to reach the right audience. You'll hear why consistency wins, which metrics matter most, and how stories outperform feature lists in every sales conversation. Listen if you are building your first repeatable lead gen motion or are tired of "pitch slap" outreach and want a human approach that actually moves deals forward. Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll actually want to listen to. Sell it. Keep it. Grow it.

15. 

    8 Oct 2025

    Ep 1 - How Growth Really Works

    Welcome to The GTM Loop Podcast with Angi Milano and Holly Glowaty. We talk about go-to-market strategies that actually work. Real stories, honest lessons, and tactical conversations on how to sell it, keep it, and grow it. From why growth is a loop (not a funnel), to navigating bank sales cycles without losing your mind, to turning compliance into a sales accelerator, we share what we've learned in the trenches with fintechs, founders, and financial institutions. Expect straight talk, practical advice, and the occasional hair flip. If you're building, selling, or scaling in fintech and beyond, this is the GTM podcast you'll actually want to listen to. Sell it. Keep it. Grow it.

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