Proposify Biz Chat

Advice 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

A 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 Kyle’s unorthodox introduction to learning how to handle rejection and pitch with confidence.   The original show can be found here: https://bit.ly/2rUQLc2.

A 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.

Part 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.

A 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.

A 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.

A 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 post on our website here: https://bit.ly/2U18ysc

Qualifying 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

Moving 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

A 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. 

A 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.  Read Kyle’s full-length blog post on our website here: https://bit.ly/2GkwWzf

A 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 they still have some value to offer your company. Read Kyle’s full-length blog post on our website here: https://bit.ly/2LfRgWF.

Every 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

A 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 post on our website here: https://bit.ly/2Ygr2WU.

Sales 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

Before 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.

There’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.

For SaaS companies who operate on recurring revenue and subscription business models, a healthy ongoing customer relationship is one of the surest ways to maximize lifetime value and minimize churn. In this episode of LTV, part one of a two-part series, Kyle explains why a customer success (CS) strategy is crucial for SaaS businesses, which metrics best assess the success of CS, and the history of the CS team at Proposify. Read Kyle's post on Medium here: https://bit.ly/2W5uUIx

The road from struggling freelancer to successful software entrepreneur is never smooth, yet Kyle’s was characterized by a special kind of personal and professional hell. In this episode of LTV, Kyle shares the entire process of writing Free Trials and Tribulations from idea to publication. He delves into the inspiration behind the book, finding his voice as an author, and the struggle to tell his story as honestly as possible and pull no punches.  Read Kyle's full blog post on Medium here: https://bit.ly/2HV4rrM. Buy Free Trials and Tribulations: https://bit.ly/2YITX5I

Hiring a business coach is a big decision; it’s expensive, and a huge time commitment for you and your potential coach. But, a great coach can help you level-up as a founder if you find yourself at a standstill. In this episode of LTV, Kyle talks about how his business coach helps make him a better leader and what to look for in a good coach.   Read Kyle’s full-length Medium post on whether or not a business coach is right for you here: https://bit.ly/2Q57zoM