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Scaling a business definitely isn’t for the weak. I’ve spent the past six months overseeing the sales team here at Proposify as we set our sights on our next revenue milestone. And it’s been full of eye-opening, thought-provoking, and sometimes counterintuitive lessons. Here are the things that surprised me most and what I learned from them.

I have a confession to make: I have never felt like I know much about sales.

I’ve never worked a sales job once in my life. Outside of door-to-door preaching in my early life, and building two businesses, I’ve never “sold” as a career, or earned a commission cheque.

So it’s not without a healthy dose of irony that I would start a company that makes sales software that we sell to sales leaders.

In the last six months, I’ve overseen the sales team at Proposify, working daily with Daniel Hebert, our Director of Sales. …

Qualifying leads is a critical step in any company’s sales process for both the sales team and the prospective client. Here’s how we do it.

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So, you’ve got a lead in the door requesting a demo of your product.

Do you oblige and carve an hour out of your day?

Or, do you spend 20 minutes qualifying this lead to determine whether they’re even worth pursuing?

When it comes to sales, losing deals are an unfortunate part of the job. Yet, there are processes that help you assess just how far down the road you need to go before moving on and marking it closed or lost.

Qualifying leads may seem like a deal killer, but the reality is that having your lead go through a qualification process benefits both of you. …

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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.

Few things inspire as much conversation among startup founders as how to set quotas and commissions for your sales team. It can be tricky to figure out if you’ve never done it before.

I’ve employed salespeople now for three years, and over time we’ve gotten closer to figuring it out, although like any process it will always adapt and evolve as the company grows. …

How to plan your yearly offsite, what to review with your leadership team, and how they can help you hit your goals.

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One thing is universally true about founding a SaaS company. At some point in the journey, the founder has to get their head out of every department and start running the company as a whole.

For me, that stage came when Proposify had grown to the point where I didn’t really know how best to manage my time and lead effectively as CEO and co-founder.

We were growing quickly and I had to put faith in my leadership team and let them run their departments. Business coaching was invaluable in that transition.

In the early days of a startup, you’re constantly grinding. Your focus is solely on building a product people care about, getting market fit for that product, and finding the cash to keep it all going. Every day is a fight to survive till tomorrow. …

Part 2 in a series on our customer success process at Proposify

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In last week’s post, I covered the basics of customer success (CS), who you want to hire for your CS team and how to compensate them, and some key metrics to keep an eye on as you roll out a strategy.

This week, I’ll explain CS from a more tactical, day-to-day standpoint. I’ll pull back the curtain on Proposify’s onboarding and renewal processes, and highlight some signs to watch for that indicate your customers aren’t doing so well.

First, let’s dive into the specifics of the onboarding process and how getting these early interactions right can set up customers for a long and successful relationship with your company. …

Selling to large companies? Support isn’t enough, you need to invest in customer success — for their own good as well as yours.

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Over the last decade, customer success (CS) has grown to the point where it is now considered a pillar of SaaS businesses, equally as important as product, engineering, marketing and sales.

In this article, part one of a two-part series on CS, I’ll explain the history of how we built a CS team at Proposify (a team I came to lead for a little while I recruited a VP), how to implement CS strategies in your own SaaS business, and the metrics to keep an eye on to track the success of customer success.

To start, let’s be clear on what customer success actually is. …

Why I wrote a book and how I got it published

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Why I decided to write a book

Writing a book has been a dream of mine since I was eleven years old.

I can actually trace the genesis of this dream to a grade 6 school project, where I had to interview an adult who did what I wanted to do when I grew up.

I interviewed Lesley Choyce, a local author here in the Maritimes, who was kind enough to come down to Joseph Giles Elementary and take questions from an eleven-year-old. Ever since, I’ve always held onto that dream of being an author and publishing a book.

As I grew up, life came at me hard and fast, throwing plenty of punches along the way (if you read my book you’ll see what I mean). But writing that book was always in the back of my mind. And along with that desire I wrestled with the author-to-be’s eternal struggle: what do I write about? …

Plus, things to know when considering hiring one yourself.

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It’s easy to picture the titans of the corporate world as lone wolves.

Armed with fearsome intellects, razor-sharp intuition and foresight, alone on the frontiers of what’s possible in the realms of business, technology, and innovation.

Figures like Elon Musk, Steve Jobs, Mark Zuckerberg — they’re all portrayed as solitary geniuses, presiding over their tech empires with near-omniscience. You wouldn’t be alone in thinking their success was the result of a one-man show.

But that fantastical image couldn’t be further from the truth.

The reality is that behind all hyper-successful individuals exists a network of people willing to lend support, assistance, and guidance at critical times. …

Getting started with product management, and what to look for in an aspiring PM.

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So, you’ve got a great idea for a new app, mapped out a business model and a target market, and decided you actually want to start and operate a software company. But what’s the process to turn this pipedream into a functional, profitable digital product?

The early stage of a software company is all about building a kick-ass team that will help you turn your vision, or maybe the first shoddy iteration of that vision, into a scalable product.

Hiring a developer early on is a no-brainer — you need someone who can actually build the app. That person might be you, the founder, depending on your skill set. However, it’s often not enough to have just a developer on board in the early stages, no matter how talented that individual may be. …

It’s not as hard as you think, but the results can skyrocket your startup

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When I talk to founders, they often fall into one of two camps.

First, the computer science and software engineering camp; the people who have the technical chops to build a product.

Second, those with a sales and marketing background or deep industry-specific knowledge; for example, a lawyer building an app for lawyers.

What I rarely find is a founder with experience and deep knowledge in design and user experience.

As SaaS continues eating the world, the best products and the fastest growing companies are the ones creating an incredible user experience. …


Kyle Racki

CEO of Proposify, Author, Speaker, Investor

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