Kyle Racki - Podcast Details

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The Remote Work Tribe PodcastThe Remote Work Tribe Podcast: Kyle RackiIn this episode of the Remote Work Tribe podcast, we chat with Kyle Racki, Co-Founder and CEO of Proposify. We talk about his journey as a founder, leadership and coaching strategies, the importance of having the right people in the right roles, AI, and more.Episode Timestamps:What is the most exciting thing Kyle is doing right now? (0:32)How has his role as a co-founder evolved? (1:20)What led Kyle to delegate less and jump back into the business? (2:46)How did COVID and the tech boom impact Proposify's growth? (4:46)Knowing what he knows today, what would...2025-05-0139 min

Remarkable Regional BusinessKyle Racki - ProposifyRemarkable Regional Businesses - Episode 22 Guest: Kyle Racki Business Name: Proposify Website: https://www.proposify.com LinkedIn: https://www.linkedin.com/in/kyleracki Topics Covered / The Journey of Proposify Kyle Racki shares how he transitioned from a freelance designer and agency owner to the founder of Proposify. He talks about the early frustrations of creating proposals manually and how that led him to develop a SaaS solution that streamlines and improves the proposal process for businesses. / Building and Scaling a SaaS Business Proposify started as a small, bootstrapped venture...2025-03-171h 04

Dial it inS3 Ep03 Leadership Lessons: Kyle Racki on Managing Growth, Layoffs and Company CultureIn this episode of Dial It In, Trygve Olsen and Dave Meyer have a conversation with Kyle Racki, the CEO and co-founder of Proposify. They explore various themes including the importance of the fourth quarter for business optimization, Proposify’s integrated CRM features, and the benefits of machine learning for proposal management. Kyle reveals Proposify’s journey from idea to a leading SaaS company, emphasizing the value of exceptional customer support and the introduction of Proposify Automations. The episode also covers challenges like technical debt and layoffs, alongside insights on predictive AI, automation in business operations, and maintaining brand cons...2024-10-2443 min

Unicorn LeadersEp. 15 - The Work of a Startup CEO with Kyle RackiKyle Racki, the co-founder and CEO of Proposify, Kyle helps thousands of businesses remove the bottleneck of proposals and get more visibility into the close. In true serial entrepreneur form, Kyle also co-host his own podcast, The Racki and Symes Podcast, where he discusses ideas and strategies to push through growth.Kyle got his start in marketing and design, and ran a digital agency for over five years before selling it and starting Proposify.Since then he’s amassed a wealth of experience and lessons that he shares with us in this episode.2023-03-081h 04

Scribble TalkScribble Talk Tech Leaders Podcast Episode 2 with Kyle Racki, CEO, ProposifyKyle Racki is the CEO and co-founder of Proposify, software that helps thousands of businesses remove the bottleneck of proposals and get more visibility into the close. Based in Halifax, Canada, Kyle and Proposify have won multiple awards over the years, including the EY Tech Entrepreneur of the Year for Atlantic Canada and Deloitte Fast 50. In addition to running Proposify, Kyle also works with other companies and startups as an investor and strategic coach, and sits on the board of Bright and MarsVR. He co-hosts a weekly business podcast, The Racki Symes Podcast.Support the show 2023-02-2457 min

Grit Daily Startup ShowTaking Your Business From $0 to $10M ARR - Kyle Racki - ProposifyKyle Racki, in his own words, was “raised in a cult”. As the son of devout Jehovah’s Witnesses, he was indoctrinated—and expected to indoctrinate others—from an early age."By age four, I was accompanying my parents as we went door-to-door handing out pamphlets to strangers.By age seven, I was giving 5-minute prepared sermons to the entire congregation.By the time I was in my early twenties, I was giving hour-long sermons every month.Eventually I woke up and left the cult for good."Today, Kyle is the CEO...2022-06-2316 min

Sales Strategy & Enablement by Revenue.ioIs the Proposal the Most Important Stage of the Sales Process? with Kyle RackiKyle Racki is the co-founder & CEO of Proposify. On today's episode we're talking about the importance of proposals and why Kyle believes that proposals "the most important stage of the sales process." We explore how you can differentiate your proposal to close a deal. And we dig into some of the key findings from research Kyle and his team did on winning proposals that are contained in Proposify's State of Proposals Report. Including: why 2 page proposals had the highest close rate by far. The 7 sections that must be in a winning proposal. And why images in a proposal can make t...2022-01-0738 min

Daily Sales TipsClosing the Deal: The Power of Proposal Software - Kyle Racki"Putting your proposals into some kind of a web-based platform, so that you can track the document opens and interactions, and then you'll be armed with this information. So you know when is the best time to reach out." - Kyle Racki in today's Tip 887 Do you know when is the best time to follow up? Join the conversation at DailySales.Tips/887 and learn more about Kyle and Proposify! Have feedback? Want to share a sales tip? Call or text the Sales Success Hotline: 512-777-1442 or Email: scott@top1.fm 2021-06-2403 min

The Elev8 Podcast#48 - How to Craft Your Message with Kyle RackiAs the crew takes the week off we rewind the clock and bring you an interview that Josh had with Proposify Co-founder and CEO Kyle Racki back in 2017. Kyle brings great knowledge of how to properly craft a message, and how to approach your target customer base in a way that will resonate with them. Even with 4 years since the interview took place there are many universal truths and tips that can help your business today.2021-06-2126 min

Customer ShowThe Secret To Creating Winning Proposals with Kyle RackiMost people send boring and uninspiring business proposals. In today's episode, we uncover what makes a proposal standout and actually gets you business. CEO and co-founder of Proposify, Kyle Racki joins Katelyn Bourgoin to explain: How He Turned A Pain-Point Into A Business Who He Treated His Early Adopters Like Royalty The Psychology of a Great Proposal How To Understand the True Needs Of Your Customer And So Much More Kyle Racki is the co-founder and CEO of Proposify, a modern proposal writing SaaS platform. He's also the author of "Free Trials and Tribulations: How To Build A Business While...2020-11-2634 min

Make It Happen Mondays - B2B Sales Talk with John Barrows168: Kyle Racki On World-Class ProposalsOn this week’s episode, we’re talking to Proposify’s CEO, Kyle Racki. Kyle is going to give us some steps from The State of Proposals 2020 Report so we know what it is about proposals that make people sign them. He’s also going to talk about some hot topics like RFPs, images and proposals, making it easy to buy from you, and the top performing proposal practices in business today.2020-10-1251 min

LTV with Kyle RackiAdvice from the Bumpy Road of Entrepreneurship, with Josh Chingas | Ep 31Advice from the Bumpy Road of Entrepreneurship, with Josh Chingas | Ep 31 On this episode of LTV, Kyle retraces his adventures as a SaaS founder with Josh Chingas, host of the Niche the Niche podcast. They chat about the not-so-glamourous side of entrepreneurship, the highs and lows of starting a business, and the long and bumpy road on the journey to build Proposify. The original show can be found here: https://apple.co/35fVIet 2019-12-1200 min

LTV with Kyle RackiAn Introvert's Approach to Sales: A Therapy Session, with Aggelos Mouzakitis | Ep 30A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. An Introvert's Approach to Sales: A Therapy Session, with Aggelos Mouzakitis | Ep 30 For entrepreneurs and founders, learning how to sell and close deals is as essential to the success of your business as the product or service itself. In this episode of LTV, Kyle chats with Aggelos Mouzakitis about how to obtain a sales culture when you’re not a natural-born hustler, scaling a sales mentality to navigate enterprise deals, and K...2019-12-0500 min

LTV with Kyle RackiSwimming Upstream: A Conversation about Moving Upmarket, with Collin Stewart | Ep 29A shift up-market to sell to larger companies is high on the list for most founders growing a SaaS company. Pulling it off… well that’s easier said than done. On this episode of LTV Kyle chats with Collin Stewart, co-host of the Predictable Revenue podcast, about Proposify’s move up-market and all the changes to the product, pricing, and sales process that came along with it. The original show can be found here: https://bit.ly/2OrGtZC.2019-11-2800 min

LTV with Kyle RackiThe Importance of Building Repeatable Systems into Your Business, with Mandi Ellefson | Ep 28Part of growing a business means accepting that there will come a day where it’s impossible for you to run it on your own. Your role as a founder is to build repeatable systems into your company so that it CAN operate without you. Join Proposify CEO Kyle Racki for a conversation with Mandi Ellefson, host of the Hands-Off CEO podcast, about optimizing and innovating business systems. The original show can be found here: bit.ly/346aIej.2019-11-2100 min

LTV with Kyle Racki7 Surprising Sales Lessons I Recently Learned About Scaling to $10M ARR | EP 27A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. 7 Surprising Sales Lessons I Recently Learned About Scaling to $10M ARR | EP 27 Scaling a business definitely isn’t for the weak—or those unwilling to abandon a failing process and start from scratch. On this episode of LTV, Kyle reflects on the eye-opening, thought-provoking, and sometimes counterintuitive lessons he’s learned overseeing the sales team at Proposify over the last six months.2019-11-1400 min

LTV with Kyle RackiGrowing a Sales Team from $0 to $7 million ARR, with Jeremy Chatelaine | Ep 26A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. On this episode of LTV, Proposify CEO Kyle Racki tells the story of how the company grew from $0 to $7M in annual recurring revenue and all the lessons, obstacles, and triumphs along the way. This show is taken from the B2B SaaS Web Summit, and the conversation Kyle had with host Jeremy Chatelaine. The original show can be found at this link: https://bit.ly/2NqiZnc.2019-11-0700 min

The Predictable Revenue Podcast124: How Proposify went from selling self serve deals to working with enterprise clients with CEO Kyle RackiOn this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Kyle Racki, noted author and CEO of Halifax’s Proposify. In addition to leading Proposify’s growing team through fundraising rounds, the ups and downs of startup life, and a company-wide evolution to sell bigger deals, Kyle is a trained designer, former agency head, and noted author. Throughout the pod, Collin and Kyle discuss Proposify’s move up market from servicing just small businesses to selling enterprise deals. Highlights include: Proposify...before moving up market (4:37), where did Proposify start price-wise to go up mark...2019-10-1646 min

Hands-Off CEOOptimizing and Innovating Systems with Kyle Racki EP 20In today’s podcast, Kyle Racki, founder of Proposify.com shares how he spends his time optimizing and innovating systems while his team runs the business. Listen in as Kyle shares about the Four Hour Work Week, creating repeatable systems, Gary V. and Free Trials (and Tribulations).2019-10-0341 min

LTV with Kyle RackiHow We Demo Our Product to Leads at Proposify | Ep 25A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. How We Demo Our Product to Leads at Proposify | Ep 25 Once a lead is qualified, they’re ready to see your product in action. But, not every prospect has the same pain, meaning a generic demo presentation just won’t cut it. Join me as I run through the exact demo process we use at Proposify, and explain how we ensure our prospects walk away intrigued and ready to buy. Read Kyle’s full-length blog p...2019-08-2200 min

LTV with Kyle RackiThe Exact Lead Qualification Process We Use at Proposify | Ep 24Qualifying leads is a critical step in any company’s sales process for both the sales team and the prospective client. Without it, your reps could be wasting valuable time on demos for ill-fitting leads who either won’t buy or who inevitably churn after a few months. Join Proposify CEO Kyle Racki as he walks you through the exact qualification process we employ at Proposify to identify the best-fitting leads who deserve a demo. Read Kyle’s full-length blog post on our website here: https://bit.ly/2OWVR2u 2019-08-1500 min

LTV with Kyle RackiThe Complete Guide To Moving Up-Market in SaaS | Ep 23Moving up-market is complex and challenging, but it can transform your SaaS business into a scaling empire. On this episode of LTV, Kyle talks about why you should consider a move up-market to sell to larger companies, and what challenges lie ahead. Read Kyle’s full-length blog post on our website here: https://bit.ly/2KkmgBL 2019-08-0100 min

LTV with Kyle RackiHow to Compensate Your SaaS Sales Reps | Ep 22A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. How to Compensate Your SaaS Sales Reps | Ep 22 Figuring out how to properly compensate your salespeople is one of the toughest challenges when building a scalable SaaS sales process. In this episode of LTV, Kyle lays out the cold, hard numbers and provides a roadmap for structuring quotas and commissions for SaaS sales reps. Read Kyle’s full-length blog post on our website here: https://bit.ly/2SFtbcB. 2019-07-2500 min

LTV with Kyle RackiHow to Generate Leads and Land Deals for Your Enterprise SaaS Product | Ep 21A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. How to Generate Leads and Land Deals for Your Enterprise SaaS Product | Ep 21 Landing an enterprise deal can mean hitting your entire revenue quota in one fell swoop. But are you prepared to handle the extremely long sales cycle, multiple stakeholders, and product customization typical of an enterprise SaaS deal? Join Proposify CEO Kyle Racki and Director of Sales Daniel Hebert as they break down the mechanics of a complex sale from lead to close. 2019-07-1800 min

LTV with Kyle RackiShould You Keep Rogue Salespeople On Your Team? | Ep 20A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. Should You Keep Rogue Salespeople On Your Team? | Ep 20 The rogue salesperson is a formidable force when it comes to bringing in revenue. But does their go-it-alone mentality have any place in modern sales teams characterized by teamwork and collaboration? Join Proposify CEO Kyle Racki and Director of Sales Daniel Hebert for part four of a five-part series on sales in SaaS as they discuss if the lone wolf salesperson is an endangered species or whether...2019-07-1100 min

LTV with Kyle RackiHow to Build a Scalable SaaS Sales Process from Scratch | Ep 19Every company has a sales process, but how do you know if it’s ready to scale? In this episode of LTV, Kyle is joined by Proposify's Director of Sales, Daniel Hebert, as they discuss the fundamentals aspects of building a repeatable and scalable SaaS sales process from the ground up. Read Kyle’s full-length blog post on our website here: https://bit.ly/2xuwY2H 2019-07-0400 min

LTV with Kyle RackiWhat to Look for in a Sales Enablement Manager | EP 18A podcast straight from the trenches of a startup, with co-founder and CEO of Proposify, Kyle Racki. What to Look for in a Sales Enablement Manager | EP 18 A solid sales enablement strategy only works if it’s designed to address the major bottlenecks hindering a sales cycle from optimal functioning. In this episode of LTV, Kyle is joined by Proposify's director of sales, Daniel Hebert, as they clarify exactly who you want to hire in a sales enablement position depending on the unique challenges facing your sellers. Read Kyle's full-length blog po...2019-06-2700 min

LTV with Kyle RackiSales Enablement: What It Is and Why It Matters | EP 17Sales enablement has evolved from a byproduct of established sales roles into an integral function of a robust sales process. Yet as it continues to develop, it has escaped a concrete definition. In this episode of LTV, Kyle is joined by Proposify’s Director of Sales Daniel Hebert as they shed some light on sales enablement and how this important process fits into a SaaS company's sales strategy. Read Kyle’s full-length blog post on the Proposify blog here: https://bit.ly/2MYGxS8 2019-06-2000 min

LTV with Kyle RackiThe Process Behind Our Annual Offsite Planning Session | EP 16Before a SaaS company can truly scale, every founder needs to transition from an entrepreneur with a say in every departmental decision to CEO running the company holistically. In this episode of LTV, Kyle explains how this process needn’t be a shot in the dark and how annual planning sessions with your leadership team are the perfect opportunity to map out the future of your business. Read Kyle’s full-length blog post on Medium here: https://bit.ly/2MHxRiH.2019-06-1300 min

LTV with Kyle RackiHow Our Customer Success Team Achieved Negative Churn For Four Consecutive Months | EP 15There’s a good reason negative churn is the holy grail of SaaS. When effective customer success (CS) strategies pay off, the result is exponential revenue growth, even when sales are slow. In this episode of LTV, part two of a two-part series, Kyle breaks down the day-to-day operation of the Proposify CS team and exactly how CS minimizes churn. Read Kyle's full-length post on Medium here: https://bit.ly/2WlWbqa.2019-06-0600 min

Run a Profitable GymEpisode 171: Free Trials (and Tribulations) with Kyle Racki Episode 171: Free Trials (and Tribulations) with Kyle Racki Today we are joined by Kyle Racki of Proposify, based in Halifax, Nova Scotia, Canada. Proposify is a company that helps thousands of companies improve their sales workflow and win new customers. Kyle has recently written a book, “Free Trials (and Tribulations),” and today we dive into his new book and learn more about Kyle’s experiences as an entrepreneur. Kyle is a really amazing guy who not only runs Proposify but is also an angel investor, speaker, and host of his own podcast. In the early...2019-06-0637 min