B2B SaaS Sales Video Series | Proposify

There’s sales.

Then there’s sales for SaaS.

Not all that long ago, sales was a one-size-fits-all business activity. No matter the product, no matter the industry, the same playbook applied.

If you were a buyer interested in a product, all of the information you needed to make a decision came from the salesperson.

In other words, the company held all the cards.

A distinct sales methodology emerged as a result of that dynamic. One that put the focus on the company first and the buyer second. And the type of salesperson that methodology produced? Well, modern sellers are still dealing with the stigma of the 20th century salesman.

Fast forward to today, and things have changed.

Take Me to the First Video, Already!

The rise of SaaS (Software-as-a-Service) flipped the buyer/seller dynamic. Now, the deck is stacked in the buyer’s favour.

Buyers are armed with almost endless ammunition to power purchasing decisions. Educational blogs, peer-to-peer review platforms like G2, social media, free trials; there are countless resources to turn to before a buyer even thinks to talk to a salesperson.

Companies who dominate B2B SaaS sales do so because they put the customer at the centre of their sales strategy. They succeed because they address the fundamental SaaS industry challenges:

  • Highly technical products sold on a recurring revenue basis
  • Complex, high-touch, and lengthy sales cycles with multiple stakeholders
  • Standing out in extremely competitive and often saturated markets

Most importantly, successful sales teams rely on a systematic, repeatable, and scalable sales process.

In these videos, we’ll give you an introduction to building, maintaining, and optimizing your own.

Our mission at Proposify is to help sales teams close more deals. And we’ve seen A TON of deals in our time. To date, our platform has helped close over $2 billion of won business for our customers...and counting.

Join our CEO Kyle Racki and Director of Sales Daniel Hebert as they discuss what sets top B2B SaaS sales organizations apart. They cover:

  • How to equip reps with the tools and training they need to sell more effectively
  • Bridging the divide between sales and marketing and aligning both departments’ goals
  • What SaaS reps are really selling (hint: it’s not just software)

And a whole lot more. Let’s jump in.


Who are these guys?

Kyle Racki

Kyle Racki

CEO & Co-Founder

An entrepreneur for more than 10 years, the co-founder and CEO of Proposify, and a graduate of the school of hard knocks with a major in street smarts, Kyle is focused on empowering companies to improve their sales so they can reap the benefits that come with a thriving business. From selling 6-figure projects to closing 8-figure investment deals, Kyle knows how to close.

Dan Hebert

Daniel Hebert

Director of Sales

Dan helps B2B companies generate pipeline and revenue. He started his career establishing influencer relationships for a tech startup and quickly developed into a go-to-market leader in both marketing and sales roles. He’s built content systems, marketing and sales processes, and enablement strategies from scratch. Now Proposify’s director of sales, he’s building our sales organization and helping customers scale theirs.


Video 1 >

Sales Enablement: What It Is and Why It Matters

Sales enablement is a relative johnny-come-lately to the world of B2B sales. Only in the last decade has it emerged from legacy sales roles and evolved into a stand-alone discipline.

And it’s evolving quickly. Over the past five years, the prevalence of organizations with a dedicated sales enablement strategy has grown from fewer than 20% to over 60%*.

It’s also no coincidence that the likelihood that a company employs a sales enablement strategy increases proportionally to that company’s revenue. In other words; the more money a sales team brings in, the more likely they are to have someone (or an entire team) devoted to enablement.

As B2B SaaS sales grow increasingly dynamic in a market that demands individual attention and specialization, the playbook is changing. And sales enablement professionals are playing a title role in rewriting it.

For SaaS companies, an effective sales enablement professional needs to possess a unique, multi-pronged skill set that combines both a technical and personal mindset:

  • Communication: The ability to understand highly complex technical topics and articulate these topics in plain English with accuracy and concision.
  • Coaching: Teaching reps to efficiently communicate these points to their prospects and customers.
  • Diplomacy: Maintaining the interdependency and effective collaboration between the sales department and the rest of the company comes with the turf.

In this video, Dan and Kyle provide a definition for sales enablement in the context of a SaaS company. They offer a glimpse at what a sales enablement strategy looks like on the ground at Proposify. And, they make the case for why sales enablement is quickly solidifying its place as a core function of a modern sales team.

*Source: CSO Insights – 4th Annual Sales Enablement Report

Video 2 >

What to Look for in a Sales Enablement Manager

A good sales enablement strategy is like oil to the sales machine.

It reduces friction in the sales funnel, allows leads to progress along the buyer journey with greater ease, and enables (deliberate word choice here) sales reps to perform their jobs more efficiently.

But, not every sales engine squeaks the same.

So sales enablement, by necessity, takes many different forms—it’s far from a one-size-fits-all approach. What your strategy ends up looking like depends entirely on two distinct factors:

  1. The maturity of your sales process
  2. The bottlenecks that are holding your reps back from closing more deals.

The success of your strategy depends on how well it addresses these factors. Which makes it tough to find the right person to execute it.

In this video, Kyle and Dan discuss some common hang-ups SaaS sales reps are up against. They then break down the exact skills, background, and expertise required in a sales enablement pro to address specific challenges like:

  • Bridging the gap between sales and marketing, and ensuring reps have fast, easy access to up-to-date sales content
  • Selling a complicated product or service, and coaching reps to consistently communicate its value to potential customers
  • Handling large sales teams and developing onboarding programs that get new reps to terminal velocity as quickly as possible.

Video 3 >

How to Build a Scalable SaaS Sales Process from Scratch

In the early days of a SaaS company, achieving product/market fit is like finding the holy grail.

But, it’s still not enough.

To truly succeed and grow as a company, founders and sales leaders need to develop a predictable, repeatable, and scalable sales process. This will become the blueprint reps follow as they sell your product or service, and the machine new salespeople are plugged into as they join the team.

Building a sales process is a complex challenge for any company, and one that requires a lot of trial and error. SaaS companies face the additional task of addressing one of two characteristic (and contradictory) challenges that depend on the nature of your product or service:

1. Convincing and persuading prospects to pick your solution in a marketplace saturated with similar solutions from higher-profile competitor companies


2. If you’re creating a brand new product category, generating the interest and demand required to convince people to buy what you’re selling

Whether your sales process—and, by extension, your revenue—scales or flounders depends on how well you address these obstacles.

Here, Kyle and Dan offer an introduction to a gargantuan topic. They offer insight into creating a SaaS sales process based on their own experience, and what it takes to get a repeatable process off the ground and into action. They cover:

  • How to enter the market with a minimal viable product (MVP)
  • The importance of understanding target buyers and qualifying leads
  • Deciding when to segment your sales team, and whether to segment at all

Video 4 >

Should You Keep Rogue Salespeople On Your Team?

If you’ve spent a decent amount of time immersed in the world of sales, you’ve most likely crossed paths with the rogue salesperson.

They can be a formidable force when it comes to bringing in revenue. Their high-performing, hard-charging nature can be attractive to a sales leader, especially in the early days of a company when driving revenue and hitting targets is top of mind.

But, renegade sellers are difficult to manage and often ignore established processes to go it on their own. Worse still, their solo nature may jeopardize the collaboration and teamwork characteristics of a modern sales team. Not to mention their contempt for the sales process you’ve been labouring to build.

Cowboy sellers can be great for an organization’s bottom line, but sales leaders have a tough decision to make when deciding whether to bring them on.

  • Are their deal-closing and target-hitting abilities too good to ignore?
  • Or do they put the culture of the sales team at risk?

In this video, Dan and Kyle discuss the utility of the lone wolf salespeople. Are they an endangered species? Or do they still have some value to offer your company?


Video 5 >

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

Landing enterprise accounts are an attractive proposition to sales leaders in SaaS companies. The benefits of closing these deals are pretty clear:

  • A big pay day and smashed quotas
  • Landing large account with lots of expansion opportunity and a lower risk of churning
  • Brand recognition (and bragging rights) that go hand-in-hand with having a well-known company as a client

But, if it were easy, everyone would be doing it. Enterprise accounts are the white whale of SaaS sales for a good reason: They’re elusive, and the process to get deals to close can be long, complex, and incredibly demanding.

There’s often months of back-and-forth between multiple decision-makers, gatekeepers who will shut the deal down at a moment’s notice, and significant resources focused on a single deal which may or may not come through.

On top of all that, many SaaS companies leave the hardest job in sales to their most inexperienced reps. Junior salespeople in SaaS companies are tasked with prospecting high-level managers, directors, and executives at enterprise companies—individuals with decades of experience.

Kyle and Dan break down some tips and recommendations for navigating complex deals with enterprise customers. They cover:

  • The motivations of enterprise buyers and how to play to those motivations during lead generation and throughout the deal
  • How to identify the different players in an enterprise deal and how to appeal to each decision maker
  • The viability of the current B2B SaaS enterprise sales model which leaves salespeople at the start of their career left opening doors and generating interest with seasoned pros.

The Tool That Helps SaaS Teams Win More Deals

SaaS is an industry in a constant state of flux. Standing out in a crowded market and winning new business is tough.

Success in B2B SaaS sales ultimately depends on the viability of your process.

A good sales process acts like a road map; it’s a blueprint that details exactly how to guide a prospective buyer on the journey from lead to close.

When the process is sound, the sales machine is firing on all cylinders. That means:

  • Reps contribute to a healthy team culture and have easy access to the training, resources, and tools they need to own their jobs
  • Sales’ and marketing’s goals are aligned, and they work together to deploy a powerful and consistent brand experience
  • The customer sits at the centre of the sales process and their experience is uniformly exceptional throughout the entire journey

But even the best processes are always being refined and optimized—there’s always room for improvement. That’s where we come in.

Proposify makes it easier for modern sales teams to create, send, track, and e-sign winning proposals, contracts, and agreements.

Try Proposify for 14 days for free and keep your prospects engaged and delighted at every step of your sales process, all the way through to the moment they sign.

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