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Kyle Racki
Co-founder and CEO of Proposify. Author of the book Free Trials & Tribulations. Outside of work, Kyle loves playing with his wife and 3 sons, picking away at his Telecaster, and attempting to surf. Connect with me on LinkedIn.
Read more from Kyle Racki:
How to Ask For the Sale
You've put in the work, you know your solution is a good fit for your prospect, and you’re eager to get the project off the ground. But before you can sign, seal, and deliver the deal, one final obstacle stands in the way: the dreaded closing conversation where you ask for the sale. In this post, I’ll walk through the 10 top takeaways from my conversation with sales legend and master closer, John Barrows.
The Best Cold Email I’ve Ever Received (and How to Write Successful Cold Emails)
'Cold email' is an ugly term. No one wants to send them, no one wants to receive them. But, when used correctly, cold emailing can be a powerful lead generation tool for your business. In this post, I break down one of the best cold emails I've ever received, the reasons why it worked so well, and my top tips for writing and sending your own effective cold emails.
There’s a ‘Black Box’ in Your Sales Process. Here’s How to Remove It
You wouldn’t send leads through your marketing site without tracking and analytics, right? So why are you still in the dark about what happens in your sales process after your reps send a proposal? I’m sharing the two critical things SaaS sales leaders need to shine a light on to optimize your closing process.
7 Surprising Sales Lessons I Recently Learned About Scaling to $10M ARR
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.
How We Demo our Product to Leads At Proposify
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.
The Exact Lead Qualification Process We Use at Proposify
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. I’m going to take you through our exact qualification process we employ at Proposify to identify best-fit leads who deserves a demo.
The Complete Guide To Moving Up-Market in SaaS
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.
How to Compensate Your SaaS Sales Reps
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.
How to Generate Leads and Land Deals for Your Enterprise SaaS Product
Landing an enterprise account can mean hitting your revenue quota in one fell swoop. But are you prepared to handle the multiple complexities of an enterprise SaaS deal? Here’s a look at the mechanics of a complex sales process from lead to close.
Should You Keep Rogue Salespeople On Your Team?
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.
How to Build a Scalable SaaS Sales Process from Scratch
Every company has a sales process, but how do you know if it’s ready to scale? In part three of a special five-part series on sales in SaaS, Proposify’s CEO Kyle Racki is joined by Director of Sales Dan Hebert as they discuss how to build a sales process from the ground up and the fundamental components to keep in mind when doing so.
What to Look for in a Sales Enablement Manager
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, part two of a special four-part series taken from our podcast, LTV with Kyle Racki, Proposify CEO Kyle Racki is joined by our 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.
Sales Enablement: What It Is and Why It Matters
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 special five-part series taken from our podcast, LTV with Kyle Racki, Proposify CEO Kyle Racki is joined by our director of sales Daniel Hebert to shed some light on sales enablement and how this important process fits into a SaaS company's sales strategy.
Why Your Agency Needs a Client Retention Strategy
Retaining clients will help scale your agency much more effectively than trying to acquire new ones. So how do you keep the clients you have and maintain a happy and mutually beneficial client/agency relationship?
The 4 Types of Serial Entrepreneurs and Why I’m Not One of Them
Some people who describe themselves as serial entrepreneurs think of the term as a badge of honour, but I’m not convinced. Here’s what I’ve learned about entrepreneurship that’s changed the way I think about running multiple businesses.
Should You Charge Enterprise Clients More Than SMBs?
If you’re used to selling to SMBs, the enterprise sales process can be a bit of mystery. Is your pricing strategy too low? Too high? Here are four reasons why you should increase your enterprise quotes.
Proposify 2 is Here! (plus exciting investment news)
For more than a year, our team has been grinding away, building the next evolution of Proposify. It’s fast, smooth, and easier to use, plus it comes loaded with some cool new features to celebrate. We can’t wait for you to try it.
How to Productize a Service to Work Less and Earn More
Running a service company doesn't mean you need to sell it like a service. Some service companies leverage the power of product marketing to scale their business. Here’s how some of the best company's productize their services.
Ramp Up Your Team’s Sales Skills With This Closer’s Toolbox
Sales is a cut-throat industry, and even more so when you’re first starting out. To win over clients and blow your competition out of the water, you need sales skills, but you also need a game plan and tricks in your sales toolbox.
How to Write Better Microcopy to Improve Your UX
Microcopy - the small bits of text on your website, app, or product that instruct and alleviate the concerns of users - isn’t just important; it’s crucial to good product design. It’s not enough just to have microcopy; you need to know how to use it properly.
2017: A Year in Review at Proposify, and What’s Next in 2018
2017 was a big year for Proposify, and I hope it was for our readers and customers, too. Here’s what we did, what we learned, and what’s in store for 2018.
How to Start an Agency That’s Set for Success
If you’re a successful freelancer with a vision to start a design or marketing agency, you’re about to embark on what will likely be one of the biggest emotional roller coasters of your career. Running an agency can be fun and rewarding, but also stressful and terrifying. I know because I’ve been there. Here are my 10 best tips to start your agency on the right foot.
Metrics that Matter: 7 KPIs to Keep Your Agency Profitable
What are the metrics you need to stay on top of in order to keep your business in the black? I'm sharing the most important KPIs and how to track, report, and act on them.
Why Kids Should Be Taught Entrepreneurship Early On
It’s clear the world needs more innovation and more entrepreneurs. So how can we nurture that next generation of doers and dreamers? Here's my story of lifelong entrepreneurship, plus the problem with school and how to start teaching kids the skills they need to start their own businesses.
How to Choose the Best CRM for Your Business (Including Our Favourite)
With so many products in the market, choosing CRM software that’s right for your business and sales team can be difficult. In this post, I share our criteria for choosing a CRM that’s best for Proposify, provide a breakdown of the nine products we reviewed, and reveal which CRM we chose as our winner.
How to Pitch like a Pro and Close More Deals
Your pitch deck needs to be more than just pretty pictures. You need to understand how your client’s brain reacts to pitches and makes decisions. Here’s how to improve your pitch and close more deals.
How to Be a Sh***y Client and P*** Off Your Agency
If someone at your marketing agency forwarded this blog post to you in a joking manner, chances are they’re actually serious, and you’ve been a shitty client. You probably aren’t aware that your behaviour is sabotaging your agency’s ability to do great work; work that, in turn, could deliver valuable results for your business. Let's turn it around, shall we?
Tired of Competing on Price? How to Use Value-Based Pricing to Boost Your Bottom Line
Losing a potential new deal because someone else offered a lower price is painful. Sadly, this is a common casualty in agencies where clients sometimes view things like a website build as a commodity rather than a service. Value-based pricing can help you transcend the unwinnable price war and scale your business.
Firing an Employee the Right Way
Firing an employee is the elephant in the room at any company. No one wants to talk about it, think about it, or actually do it. But sometimes, in the best interest of your business, it needs to be done. Here's how to do it right—or even better, not have to do it at all.
How to Get Clients to Pay Your Invoices On Time
One of the biggest challenges of running a service business is managing cash flow. Expenses like payroll, rent, utilities, and software all come out of your bank account every month like clockwork, but clients can sometimes take their sweet time to pay their invoices. Here’s how to make sure your money comes in a little more on the regular.
How We Hired Inbound Sales Reps
For the first two years of Proposify, we didn’t have a structured sales process or a dedicated sales team. Six months ago we decided to hire two inbound sales professionals, and it’s had a huge effect on our business. Here’s why we did it, how we did it, and what we’ve learned in the process.
7 Sales Tools Every Inbound Team Needs (Plus Our Personal Favs)
Software may not actually do the selling for you, but it sure makes the job easier. Here are the tools we used at Proposify to simplify and automate parts of our sales process and how we tied them all together.
How to Sell an Agency and Find the Right Buyer
It was one of the most important decisions of our lives: do we sell the company that’s been our source of livelihood for five years? The process took an arduous and brutal ten months but looking back both my business partner and I can say with confidence that selling our web design agency was one of the best decisions of our lives. Here's what I learned the hard way.
How to Scale Your Agency
If you own a small agency and you want to be more profitable, there’s nowhere to go but up. You have to scale your business. We’ve got nine steps to help you get your agency, and your team, on track for growth.
How to Qualify a Lead Before Sending a Proposal or RFP Response
Want to know the ONE thing, THE most important thing, that will make your proposal process more successful? It’s this: not every sales lead deserves a proposal. Here's how to make sure only you're only sending proposals to highly qualified leads.
Why You Shouldn't Pay Finder’s Fees for Business Referrals
Finder’s fees can be a murky area. Is paying money to someone for referring a new buyer, customer, or investor just good business manners? Or is it a bad business decision for your agency? Here’s why I don’t think it’s the best way to scale a business, plus the few exceptions to my rule and what to do instead.
When to Hire In-house vs. Outsourcing to Freelancers for your Agency or Startup
When you’re starting out building an agency or startup, it can be costly to hire a team right out of the gate. Plus it might take awhile to understand what kind of full-time resources you’ll need long term. It’s important to find the right balance between hiring permanent employees and contracting freelancers at the right time.
The Two Types of Marketers You Need on Your Marketing Team
All marketers are not created equal and you don’t want them to be. Depending on their strengths and expertise, they bring different skills to the job and you need that range to make an effective impact. So what kind of marketers do you need to hire when building your team? Here’s what we did at Proposify.
Should You Join an Agency Partner Program?
More than ever before, agencies are pivoting to focus exclusively on one software platform, offering consulting, training, and implementation for customers of that software. As someone who has both been an agency partner and offers an agency partnership program through Proposify, I’ll explore both the benefits and drawbacks.
Agency Website Do’s and Don’ts: Are You Making These Design Mistakes?
Even great agencies, ones who do smart work for their clients, sometimes have the worst websites. It seems to be a classic case of “the cobbler’s kids have no shoes.” Too often agencies don’t practice what they preach to their clients, instead putting up bland, generic websites that never get optimized for conversion and are rarely updated. We review the best and worst of agency website design so you can atone for your online sins.
13 Tips to Generate Leads from Conferences, Trade Shows, and Events
The term ‘trade show’ likely conjures up visions of endless avenues of blue drapes, promotional stress balls, blank-faced exhibitors, and enough lanyards to lasso the entire Texas Stampede Rodeo. But what it should make you think of is ROI. Here are tips to get the most out of your next trade show. (And by ‘most’, I mean LEADS.)
How to Generate New Leads for Your Sales Funnel, Fast
You look at your sales pipeline and notice that it’s starting to dry up. Deals that were on the table have either closed or gone cold. If you don’t get some new sales leads in the door soon, shit’s going to hit the fan. We’ve all been there. I know I have. Here’s how to jumpstart your sales funnel and get new business in the door.
A Deep Dive Into Our New User Onboarding Process
How do you guide a new user to succeed using your product? It’s a question we often ask ourselves as it’s critical to retention and growth. We recently redesigned our user onboarding from the ground up and we’re sharing our process in the event it helps as you design your own product or service.
9 Ways to Use Sales Psychology to Close More Deals
Consumer psychology studies are not only fascinating, they can help you write better business proposals and ultimately close more deals. Here are nine smart studies to help your sales.
Hiring Agency Developers vs Startup Developers: 3 Things to Consider
Hiring the right kind of developer is a critical decision and it changes depending on whether you run a product or a service company. Here’s what you should keep an eye out for during the hiring process.
How to Onboard New Clients for a More Profitable Agency
You’ve landed a new client, they’ve signed on the dotted line and everyone’s ready to start that juicy new project. Here are some onboarding best practices to start your relationship out on the right foot, deliver value early, and retain this client profitably for years to come.
8 Lead Magnet Ideas to Generate Sales For Your Digital Agency
You may recommend lead magnets to your clients, but are you using one yourself? Here’s how your digital agency can develop lead magnets that generate sales, plus 8 formats and ideas to get you started.
Think Your Business is Successful? 5 Ways to Not Mess Things Up.
It’s easy to take your eye off the prize when business is booming. Here’s what to look out for so you don’t fall backwards.
Need Sales, Feedback or Business Advice? One Simple Rule For Effective Cold Outreach
Connecting with people for sales, advice, feedback, and partnerships is paramount to running a successful business. Here’s how to reach out to strangers in a way that’s respectful and gets a response.
Stop Hustling and Grinding. Start Working Lazier and Smarter
If you talk to most entrepreneurs these days, they’ll proudly announce how long and hard they hustle 24/7 to “kill it”. Here’s why that’s not healthy for you, or your business.
Why Your Small Business Needs a Team Playbook (And a Sneak Peek of Our Own)
Employee playbooks aren't just for big businesses. Even small companies benefit from documenting and sharing their process. I'm sharing our Proposify team playbook-in-progress to inspire you to create your own: what to include, what not to include, and how to make sure it continues to evolve over time.
Going after that Big, Public Sector Client? 4 Steps to Make it Profitable
Working with government clients is very different from working with private companies. Here are four things to consider to battle the red tape and bureaucracy that can ruin a public sector project's profitability.
How We Streamlined Hiring (& Found Kick Ass Talent)
We started out last year with about 200 paying customers, and by the beginning of 2016 we were at nearly 2,000. We were growing fast and needed people to keep up. This is how we painlessly grew our awesome team from 8 to a thriving 13 in three months.
Why We’re Not a Remote Team
Read any article from the tech world these days and you’ll find the consensus is that remote companies are the way of the future. Here’s why Proposify has chosen the more traditional path.
Quoting App Builds: Everything I Wish I'd Known When I Started
Building digital experiences on behalf of your clients is one thing, profiting from the work is another. Here’s how to put something out into the world that works, makes your client happy, and makes sure you don’t lose your shirt.
Building an Internal Product? 5 Steps to Avoid Certain Death
If you run an agency you’ve likely been tempted to build, or have already built, your own software product between client projects. I’ve been there myself — and that’s why Proposify exists today. Here I share how to do it right to avoid failure.
How Agencies Can Create a Repeatable System for Generating Leads
Trapped in the endless cycle of feast or famine? Here’s my suggestion for a sales system that consistently delivers new leads without wasting time on coffees with unqualified prospects.
7 Activities Business Owners Should Do Every Day
This time of year entrepreneurs are often thinking about where to take their business in the next year. But even more important is asking yourself how exactly you’ll get there. That’s the hard part, and that’s what I’m asking myself. Here’s a look at the day-to-day tasks that I’m focusing on to make my company even stronger.
We Just Launched The Definitive Guide to Going Freelance
Becoming a freelancer is a huge step, and one that often brings huge rewards to those who have the courage to make the leap. But there are a lot of pitfalls to avoid and lessons to learn from so your experience of being a freelancer is as painless as possible.
10 Ways To Keep Your Project Manager Happy
Project managers: the most powerful, and yet under-appreciated, person in a creative agency. Here's how to say thank you, show some appreciation, and stay on your PM's good side while they're herding all those "cats".