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

An Introvert's Approach to Sales: A Therapy Session, with Aggelos Mouzakitis | Ep 30

Dec 5th, 2019 28m 9s

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 a

Swimming Upstream: A Conversation about Moving Upmarket, with Collin Stewart | Ep 29

Nov 28th, 2019 47m

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 Rev

The Importance of Building Repeatable Systems into Your Business, with Mandi Ellefson | Ep 28

Nov 21st, 2019 41m 37s

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 Proposif

7 Surprising Sales Lessons I Recently Learned About Scaling to $10M ARR | EP 27

Nov 14th, 2019 13m 34s

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 unwil

Growing a Sales Team from $0 to $7 million ARR, with Jeremy Chatelaine | Ep 26

Nov 7th, 2019 51m 50s

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

How We Demo Our Product to Leads at Proposify | Ep 25

Aug 22nd, 2019 10m 4s

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 pro

The Exact Lead Qualification Process We Use at Proposify | Ep 24

Aug 15th, 2019 11m 43s

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 ch

The Complete Guide To Moving Up-Market in SaaS | Ep 23

Aug 1st, 2019 19m 47s

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 a

How to Compensate Your SaaS Sales Reps | Ep 22

Jul 25th, 2019 11m 5s

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 whe

How to Generate Leads and Land Deals for Your Enterprise SaaS Product | Ep 21

Jul 18th, 2019 15m 3s

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

Should You Keep Rogue Salespeople On Your Team? | Ep 20

Jul 11th, 2019 7m 47s

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 d

How to Build a Scalable SaaS Sales Process from Scratch | Ep 19

Jul 4th, 2019 14m 39s

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 scalabl

What to Look for in a Sales Enablement Manager | EP 18

Jun 27th, 2019 11m 23s

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 bottl

Sales Enablement: What It Is and Why It Matters | EP 17

Jun 20th, 2019 12m 37s

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 Propos

The Process Behind Our Annual Offsite Planning Session | EP 16

Jun 13th, 2019 15m 55s

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

How Our Customer Success Team Achieved Negative Churn For Four Consecutive Months | EP 15

Jun 6th, 2019 11m 42s

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,

When to Build a Customer Success Department (and How We Did It) | EP 14

May 30th, 2019 14m 45s

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-par

The Story Behind My Book, Free Trials and Tribulations | EP 13

May 23rd, 2019 10m 4s

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 Tr

Why I Hired a Business Coach | EP 12

May 16th, 2019 7m 35s

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 tal

How to Deploy Product Management in Your Startup | EP 11

May 9th, 2019 15m 33s

LTV with Kyle Racki Your first decisions as a software founder should revolve around transforming your unvarnished app into a functional, profitable, and scalable digital product. In this episode of LTV, Kyle defines product management, explai

How Early-stage Founders Can Create a Killer User Experience (Without Hiring a Ux Designer) | EP 10

May 2nd, 2019 9m 59s

LTV with Kyle Racki For more info: https://bit.ly/2py685O Today’s fastest growing companies are the ones creating an incredible user experience. We all have our favourite products, but what is it that makes using them so seamless and enjoyable?

Do You Actually Want to Own and Operate a Software Company? |EP 09

Nov 29th, 2018 5m 35s

LTV with Kyle Racki For more info: https://bit.ly/2py685O Even with a blockbuster idea, your app won’t make money overnight. Are you willing to devote years to building your product, and eventually running a software company? In this episode, K

Early Stage Founders: Sales Will Solve (Almost) All of Your Problems | EP 08

Nov 22nd, 2018 13m 22s

LTV with Kyle Racki For more info: https://bit.ly/2py685O You finally have a product to market, and that’s good news because your bills are piling up fast. You’ve got two options to keep the company on its feet: hunt VC cash, or make some sales

CEOs, Are You Prepared for War? | EP 07

Nov 15th, 2018 7m 17s

LTV with Kyle Racki For more info: https://bit.ly/2py685O If you’re a CEO you’re likely in one of two camps: a long-term planner who keeps an even keel, or an aggressive decision maker who isn’t afraid to rock the boat. Tune in to hear why Kyle