LTV with Kyle Racki

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

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, explains its importance in the early stages of a startup, and outlines what to look for when hiring a product manager.

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? In this episode, Kyle sheds some light on the supposedly dark art of UX, and digs into the fundamentals of designing a great user experience. Read Kyle’s full-length Medium post on running a software company: https://medium.com/@kyleracki/2f868510651

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, Kyle explains why apps don’t make you get rich quick, and offers some advice to help you decide whether building an app is right for you.   Read Kyle’s full-length Medium post on running a software company: https://blog.kyleracki.com/do-you-actually-want-to-own-and-operate-a-software-company-1e0b7a694412

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 calls. In this episode, Kyle makes a case for why founders should strive to be the best salesperson in their company, and why drumming up customers in the early days is more important than inking investors.   Read Kyle’s full-length Medium post on sales advice for CEOs: https://blog.kyleracki.com/early-stage-founders-sales-will-solve-almost-all-of-your-problems-a9c9657fb38f  

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 recommends being a little of both, and how to get there. Read Kyle’s full-length Medium post on the two categories of CEOs: https://blog.kyleracki.com/ceos-are-you-prepared-for-war-998eca29ae96

LTV with Kyle Racki For more info: https://bit.ly/2py685O It’s a long journey to the top of the market, and you’ll never make it without tackling one major roadblock along the way - the competition. In this episode, Kyle shares tips on beating your rivals by harnessing your company’s strengths, and discusses how a little competition is actually good for business. Read Kyle’s full-length Medium post on getting ahead of the competition: https://blog.kyleracki.com/how-to-crush-your-competition-honestly-and-ethically-4a55de44fb1f  

A company performs best when everyone is moving in the same direction, but getting your staff on the same page can be challenging when everyone has their own priorities. A simple way to get everyone together is hosting regular all-hands meetings. In this episode, Kyle shares his formula for running all-hands meetings, and discusses the benefits they bring to his company, Proposify.   Read Kyle’s full-length Medium post on running an all-hands meeting: https://blog.kyleracki.com/how-i-use-all-hands-meetings-to-build-company-culture-32e76ee053e3  

LTV with Kyle Racki For more info: https://bit.ly/2py685O Proposify only had two dozen employees at the time, and Kyle and his co-founder Kevin Springer knew they needed reinforcements to triple their staff over the coming year. In this episode, Kyle talks about how they went about finding a killer HR manager and the value she’s brought to the growing company. Read Kyle’s full-length Medium post on hiring an HR manager: https://blog.kyleracki.com/why-we-hired-an-hr-manager-with-only-24-employees-df48a797604e 

LTV with Kyle Racki For more info: https://bit.ly/2py685O Kyle and his co-founder Kevin Springer resisted taking VC in the early stages of Proposify, reluctant to hand over control of the company. In this episode, Kyle shares what changed their mind about accepting major funding, and talks about the twists, turns, and surprises that led them to choose their investors. Read Kyle’s full length Medium post on his journey of accepting an eight-figure investment: https://blog.kyleracki.com/the-story-of-raising-proposifys-8-figure-series-a-funding-cb6b8b372c6c  

LTV with Kyle Racki For more info: https://bit.ly/2py685O We set out to redevelop our software to stave off growing competition with a better user interface. We knew it was a big undertaking, but nothing would have prepared us for the mammoth challenges it presented: burnt out developers, stressed support staff, and frustrated customers to name a few. Find out what Kyle had to say about whether the rebuild was worth it, and what he would do differently next time. Read Kyle’s full length Medium post on the trials and tribulations of rewriting Proposify 2.0: https://bit.ly/2RIszC0

LTV with Kyle Racki In this episode, Kyle weighs in on how agencies can determine whether or not it’s wise to accept equity in a startup as payment for services. He explains how to figure out the true cost of the investment, how to analyze the deal you’ve been offered, what a good opportunity looks like, and some common red flags. Read Kyle’s full-length Medium post on exchanging services for equity in a startup: https://blog.kyleracki.com/6-things-agencies-should-consider-before-exchanging-services-for-equity-in-a-startup-cb81e9ca506a See more: www.proposify.com/podcast

Host Kyle Racki welcomes listeners to LTV, formerly Proposify Biz Chat. In this show, he’ll draw from his experiences of building SaaS company Proposify to frankly discuss the challenges of scaling a business, and offer wisdom to other entrepreneurs. Download now to learn more about upcoming episodes, and hear Kyle explain the rebranding of Proposify Biz Chat. See more: https://www.proposify.com/podcast  

Read Kyle’s full length Medium post on risk and entrepreneurship. https://blog.kyleracki.com/entrepreneurs-think-differently-about-risk-6dec78fe76d6  

Proposify Biz Chat For more info: https://www.proposify.com/podcast/089

I had lunch with a founder the other day who told me that while he enjoys starting up new businesses, but doesn’t like to operate them. Once the business is making money and has people who can run it, he wants to move on to the next thing. I joked with him that he’s like the Mary Poppins of entrepreneurship. Flying through the window with his umbrella to help out a business in need, and then floating back out when everything is tickety-boo, eager to move on to the next big thing. We laughed when I suggested his future business will be called Supercalifragilisticexpialidocious.   For more information check out our blog: https://www.proposify.com/blog/4-types-of-serial-entrepreneurs

In this interview, Kyle talks about his journey from quiet, artsy kid in high school to founder of Proposify, which is aiming to hit $10M in annual revenue this year. You'll also hear how Proposify started as a side project and went from a year and a half of no growth to doubling customers every month. Plus lots of other interesting bits along the way. Proposify Biz Chat For more info: https://www.proposify.com/podcast/088 For more podcasts from Founder Chats check out: https://founderchats.com

What started as Agencies Drinking Beer and then rebranded to Proposify Biz Chat, this podcast is about to undergo another evolution. (What can we say? We like to keep things fresh.) Host Kyle Racki explains why he's moving away from guest interviews, gets real about the challenges of being a good interviewer, and hints at what's to come.

In this interview, Mandi Ellefson of The Hands-Off CEO talks about how business owners need to add more value to their services so they can charge more; why you need to sell clients on results, not your process; and the hard truth that the reason your business isn’t scaling is because it isn’t profitable enough. Mandi also warns about what happens when a business owner is stuck in the ‘doer’ mode, spending too much time actually doing their service and not enough time growing their business.

This post was inspired by a question from one of our UK readers, Dean. Dean’s a WordPress web designer who normally charges his SMB clients £4-6k for a high-end brochure-style website; no gateway, no API, no bells, no whistles. As luck would have it, Dean has a lead with a large £1Bn+ company who wants a similar kind of straightforward website. He’s wondering if he should charge this enterprise-level business with VERY deep pockets the same amount that he charges his small/medium sized business clients for the same service. For more information check out our blog post at: https://www.proposify.com/blog/charge-enterprise-clients-more-than-smbs

In this interview, Kevin Brown of Mighty Ally talks about how he ended up founding a marketing agency in Uganda, why all companies regardless of their sector can —and should—be changemakers, and how even Wall Street is getting behind the idea of integrating profit and purpose and expecting social responsibility of its corporations. He also outlines the four steps your company can take toward making ‘shared value’ a part of your brand.

John Doherty is the founder and CEO of GetCredo.com, where they help businesses find the right marketing partner to work with. He has a decade of experience in SEO across in-house roles, agencies, and private consulting.

Bastian Ernst is the founder and CEO of Wild Audience, a consulting company that uses respect-based marketing and relationship funnels to get people to act and convert. Bastian mentored at Close.io under Steli Efti and then did the opposite of most founders: he LEFT Silicon Valley to establish his start-up in Costa Rica.

Tucker Max has sold over 3 million copies of his books worldwide, and is the third writer to ever have three books on the New York Times’ non-fiction best seller list at one time. Since his nomination as one of Time Magazine’s 100 Most Influential People in 2009, Tucker went on to co-found Book in a Box – a company that has created a new way to turn ideas into books.

Takeaways Don’t replace what isn’t broken With new ways to connect with prospects popping up at an ever-accelerated rate, it can be tempting to believe everything you hear, like abandoning email marketing altogether and solely reaching out to prospects with tools like Messenger bots and social media. Dave says it’s fine to use new tools if you think they can help you gain customers, but advises not to abandon the tools that are already working for you, like email.   Relying solely on social media or new tools for Messenger can put you at risk of losing contact with interested leads should that social platform’s algorithm change. If you choose to use social media as the main source of lead generation, Dave suggests trying to capture the email addresses of at least 50% of those followers so you can still stay engaged with them and make offers, should an algorithm change occur.

Custom services, like the work of most agencies, take time, and time is a finite resource. Productizing your services can help you grow your business efficiently. The truth is, service businesses are inherently difficult to scale. Think about it: selling digital marketing or design services involves meeting with clients, learning about their business, crafting a strategy, and executing deliverables for them. This means you need to spend time up front in the sales process evaluating leads and trying to determine how much time each project will take, which takes even more time.

In this interview, Jim explains why you need a niche to stand out, how pricing higher from the beginning can lead to greater success, and why all clients should be called “customers”.

Marcus Murphy is the director of sales and monetization for DigitalMarketer, which hosts the Traffic and Conversion Summit for marketers each year. Leading an umbrella department for sales, customer success, business development, partner programs and channels, and strategic partnerships, Marcus helps restore, teach, and uplevel sales professionals.

Amara Omoregie is the director of marketing for Amara Reps, a digital agency and consultancy. Having spent 14 years in sales and another ten years in marketing, Amara helps clients by focusing on inbound leads, social media, web development, and advertising. Jason Swenk helps marketing agencies grow their businesses faster. Having worked with brands like AT&T, Hitachi, and Lotus Cars, Jason grew his digital marketing agency to multi-million dollar status before selling it after 12 years in operation. He now provides clients with valuable advice and actionable steps to follow suit.

In this interview, Sam explains the critical tasks every chief marketing officer needs to nail in their first three months in a new role, and why those first three months matter the most. He also talks about the importance of getting your sales and marketing teams on the same page.

In this interview, Mikael talks about why messenger marketing is the future, why email marketing isn’t as effective as it used to be, and how to get subscribers to your messenger bot. He also reveals the most misunderstood aspect of chatbots and breaks down why chatbot conversations sound more personal.

Making sure your leadership team is on the same page is crucial to reaching goals and scaling your business. The leadership team at Proposify recently got together for a two-day yearly planning session to ensure every department lead understands the mission, goals, we’re working toward so they could develop strategies to meet those goals for the next year. In this episode, Kyle and Kevin chat about why they decided to take the planning session out of office, how the group created Proposify’s company vision together by considering the company as a whole, first, and the qualities they want to see in each Proposify employee. They also discuss how yearly planning sessions can lead help leaders feel motivated, refreshed, and like they have a better sense of direction in leading their teams.