Kyle Racki

03/15/2023

02/08/2020

Enjoyed this week in Atlanta with my coaching/matermind group JFDI day put on by

In Atlanta we connected and visited with...

Kyle @ SalesLoft / $70M / 365 ppl
Andy @ CallRail / $50M / 200 ppl
David Cummings (Founder of Pardot / Exited for $100M, Investor in Calendly, SalesLoft, Terminus and dozens of others. $1B of value creation in less than a decade)
Eric @ Terminus / ~$40M / 220 ppl

Also met with incredible founders over dinner like Tope Awotona CEO of Calendly

Big thanks to Dan, and his crew Kelsey, Jessica, Sam, and Daniel for their hard work creating a great experience. @ Atlanta Tech Village

11/12/2019

Sales is hard.

Especially when you’re building your team, moving upmarket, and aiming to hit that next big revenue goal.

And you’ve never held a sales job.

I’m sharing 7 invaluable lessons I’ve learned from my crash course in sales leadership.

Sales is hard. Especially when you’re building your team, moving upmarket, and aiming to hit that next big revenue goal. And you’ve never held a sales job. I’m sharing 7 invaluable lessons I’ve learned from my crash course in sales leadership.

10/22/2019

Happening right now.

What you'll learn:

What You'll Learn:

Nerd alert: Processes you can put in place to ensure Account Executives are still prospecting

How AE’s can best use their existing book of business for prospecting

Prospecting vs. Closing time management

The best time (and situations) to ask for referrals

Using your customer’s stories to turn into an online personality

We’re going whip your team into shape by talking about some ways to enable Account Executives to prospect more, without losing their closing abilities.

10/16/2019

Shared some lessons about the early days of starting Proposify.

I’m Kyle Racki, CEO and co-founder of Proposify. Proposify is an online business proposal SaaS (software as a service) company that streamlines the process of creating, sending, and closing proposals, quotes, contracts, and other sales documents. We do this by making the process of crea...

10/08/2019

When you’re building a product startup you don’t go out and hire 100 engineers and then say, “ok, what are we building?”

You start with 1 or 2 engineers, talk to a LOT of customers, and iterate quickly on feedback to make your first 20 customers in love with your product.

You gradually scale up as you hit product-market fit.

It’s the same with a sales team.

Most startups who raise VC money go out and try to scale sales prematurely, often breaking out roles into prospectors and closers, and I’ve learned from experience that's the wrong approach.

Go out and hire a couple “full-stack” sales reps, listen to their calls, and iterate until you figure out who your ideal customer is, and what messaging is resonating in market.

07/16/2019

I call them cowboys/cowgirls.

AKA the lone wolf.

AKA the rogue salesperson.

Whatever you call them, these folks can bring in revenue, but at what cost?

In this post (which you can read, watch, or listen to), I chat with Daniel Hebert about whether or not you keep them on your team.

The lone wolf salesperson may crush their numbers, but what toll is their renegade approach taking on the rest of the company? Join Kyle and Dan as they discuss whether the rogue seller still has a place in a modern sales organization.

06/21/2019

What is sales enablement?

Sales enablement has evolved from a byproduct of established sales roles into an integral function of a scaling sales team at large companies.

This week I talk to Daniel Hebert, Director of Sales at Proposify about what anyone building a sales team should know about sales enablement.

📰 Read the post: https://www.proposify.com/blog/sales-enablement-what-it-is-and-why-it-matters

📺 Watch the video: https://www.youtube.com/watch?v=Ah_zbjuCivU

or

🎧Listen on iTunes: https://podcasts.apple.com/ca/podcast/proposify-biz-chat/id964525622?mt=2

Sales enablement has evolved from a byproduct of established sales roles into a vital part of a robust sales process. Proposify CEO Kyle Racki and Director of Sales Dan Hebert talk sales enablement and how it fits into a SaaS company's sales strategy

05/31/2019

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.

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

05/22/2019

Behind all hyper-successful individuals exists a network of people willing to lend support, assistance, and guidance at critical times. This can take many forms; a co-founder, a supportive partner, a mentor, an investor.

Then there are those whose objectives are far more specific, someone who’s getting paid to guide you to success: a business coach.

Deciding whether to hire a business coach is a tough call. And so it should be. It’s expensive, and a massive time commitment for both you and your potential coach.

But a successful matchup could have resounding effects on the success of your company, especially if you find yourself at a standstill, not quite sure what to do next.

I’m going to tell you about why I decided to enlist the services of a business coach. I’ll share how I knew it was the right time to do so, the difference it’s made to Proposify, and what that coaching looks like from a day-to-day perspective.

Plus, things to know when considering hiring one yourself.