Selling SaaS: How to Strategically Sell B2B SaaS


Key takeaways from the ‘Building An Always-On Prospecting Engine’ webinar with marketplace leaders in sales from 6sense, Drift, Salesloft and Shift Paradigm.

Today’s marketers are under more pressure than ever to get more value from their marketing dollars, which means they’re further scrutinizing marketing technology tools and looking for a big return on investment (ROI).

When considering which technology to add to their existing marketing stack, it can be challenging to decide which tool(s) will be the most impactful. It’s no secret that the variety of options for martech solutions has quickly become overwhelming, with Chiefmartec recently reporting that the marketing technology landscape currently includes 9,932 solutions for your buyer to choose from. If you were to sit through demos (at 30 minutes per technology vendor), that would translate into almost 2 ½ years of sitting through demos just to see who does what.

What is B2B SaaS? 

B2B SaaS is Business-to-Business Software as a Service and refers to a software distribution model where a company offers software applications to other businesses. Typically, the software is hosted on the provider’s servers and made accessible to customers through a subscription-based structure.

Overall, B2B SaaS allows businesses to leverage software applications and turn them into a service to improve their operations, efficiency, and drive growth without the need for extensive in-house development or infrastructure management.

With so many SaaS & technologies options available, how are you, as a seller, going to cut through the noise to stand out in this crowded market? How are you, as a buyer, supposed to make sense of it all? 

Shift Paradigm’s Mike Barbeau recently sat down with 3 sales mavens: Derek Levine (6sense), Amanda Georgoff (Salesloft) and Chris Lynch (Drift) for a look behind the scenes of their sales processes, including;

  • The importance of trust, timing and humility
  • What considerations they would keep in mind when making a tech investment of their own
  • How to approach the decision process to get the best return on your investment (ROI)

 Here is their advice for both buying and selling SaaS.

Cultivating Trust with Truth and Technology

Trust is defined as “an assured reliance on the character, ability, strength, or truth of someone or something”.

When we trust someone, we have confidence in them, in their honesty, their integrity, and we believe that they will do the things they say they will, and that they recognize their (and their product and or services’) abilities and strengths.

Here are a few ways to cultivate trust as a buyer and a seller:

Seller’s Perspective

  • The technology you’re selling is only important if it solves the problem your client/prospect has.
  • Be proactively transparent. Know what your product/service does well and where it could be better.
  • Have the humility to acknowledge when your prospect/client isn’t ready for your solution.
  • Do your research. Know your customers, the business and the people to whom you are selling. 
  • Be a customer of your customer to help you identify their strengths and shortcomings.
  • Share relevant customer stories and scenarios similar to theirs that showcase how your solution will solve their pain point.
  • Make time to be curious – not just about your prospects, but also about what’s happening in the industry and your customer’s industry
  • In the B2B space, your success fundamentally comes from knowing and focusing on your customer’s desired outcome. Be relentlessly focused on your customer, and don’t be afraid to posit why the prospect might need your solution. If you’ve done your research effectively, your solution should resonate.

The result of investing the time and energy to all of the above will be that it will better position you as a trusted advisor, not just to the prospect, but in your industry as well.

Buyer’s Perspective

  • Look for technology partners that aren’t just trying to sell you something, but instead, have a vested interest in your success.
  • Show up to a conversation with a potential software-as-a-service (SaaS) provider as someone who is interested in learning. Ask questions and trust the seller to teach you about their space.
  • Be transparent. Tell them what you need, what you want and which other vendors you are considering.
  • When looking to purchase new technology, set a realistic timeline that is achievable for both you and your technology partner.
  • When selecting new technology for your stack, recognize that your long-term relationship is more valuable to the seller than the short-term sale. 

Our panelists agreed that both sides need to establish trust starting in the discovery process of their relationship.

Knowing the Difference Between Technology & Business Implementation

Thomas Edison once said, “Vision without execution is hallucination.” As such, knowing the difference between a technical implementation and a business implementation is another critical component of a successful project. Both buyer and seller must keep the organizational big picture in mind during any purchase decisions.

Here are other considerations to keep top of mind when looking at implementations:

Seller’s Perspective

  • Understand what success looks like to your buyer’s organization, and what success looks like to your points of contact (POC) in their current roles. Asking these two questions will unearth critical intel to a successful project.
  • Have a clear understanding of how well your POC understands the following;
  • How well do they know their audience segmentations?
  • How aligned are their revenue processes?
  • Do they have a playbook from first touch to execution, and which tool in their stack is currently responsible for which action?
  • Be able to articulate that the initial pain and changes often required of a successful implementation will be hard, but that it will be worth it in the end. 
  • Ensure the buyer knows that you are in this together.
  • Be empathetic and realistic when setting implementation timelines. 
  • Remember – you’re only successful if your customer is successful.

Buyer’s Perspective

  • Be upfront about what you know and what you don’t yet know to get the most from your technology partner.
  • Knowing your customer journey all the way through allows you to leverage technology in creative new ways. When is the best time to serve up an offer? What signals are tipping points in a buyer’s journey? 
  • Understand what success looks like to your organization and what success looks like to you in your current role, and then share this with your technology partner.
  • Recognize that some organizational changes may be necessary for a successful project outcome. Just as you need to be a champion of change, someone on your team will need to take ownership of the tool itself. Very rarely is SaaS a ‘set it and forget it’ purchase.

If Not Now, Then When? 

Fear and, more specifically, fear of missing out (FOMO) are very powerful motivators for both buyers and sellers. For the buyer, fear of missing out translates into unattained potential and dollars left on the table. For the seller, FOMO translates into lost opportunities and the disappointment of not being able to solve for or add value to a prospect’s pain point.

Here are a few other truths about the importance of timing that the panel discussed:

Seller’s Perspective

  • Tie metrics to indecision so that your buyer understands the ROI they are missing out on by holding back on moving forward.
  • Customers do not always know what they want. It is your job to help them truly understand how their pain points are impacting the business overall. Enlighten and educate them on just how important making a decision is. Time is of the essence.

Buyer’s Perspective

  • Focus. Change is hard and requires hard work. These tools are a vehicle to change not because it’s easy, but because the return is evident when implemented correctly.
  • Become a change champion, and keep moving towards the goal. 
  • Be realistic about your timing. Do you have the time, bandwidth and budget to take this project on right now?
  • Buying technology without a plan is the worst kind of plan. Take the time to plan.
  • The right partner can help you determine the right timing and cares about your success as much as you do.
  • Think about what you are risking by not moving forward.

As you can see, there are many factors that influence a long-lasting relationship between buyer and seller. The most essential factors being trust, commitment to a shared goal, and communication. With those three factors firmly in place, both parties should feel empowered to tackle a collaborative project. Remember – you’re in this together!

Do you need support in fine-tuning your B2B SaaS sales strategy, or in understanding how to best approach a purchase decision of your own? Talk to Shift Paradigm today. We’ll help you cut through the noise.

To view a full recording of the webinar ‘‘Building An Always-On Prospecting Engine’ please visit here.



6sense reinvents the way organizations create, manage, and convert pipeline to revenue. 6sense Revenue AI captures anonymous buying signals, targets the right accounts at the ideal time, and recommends the channels and messages to boost revenue performance. Removing guesswork, friction and wasted sales effort, 6sense empowers sales, marketing, and customer success teams to significantly improve pipeline quality, accelerate sales velocity, increase conversion rates, and grow revenue predictably.


Drift®, the Conversation Cloud company, helps businesses connect with people at the right time, in the right place with the right conversation. Using the Drift Conversation Cloud, businesses can personalize experiences that lead to more quality pipeline, revenue and lifelong customers. Drift brings Conversational Marketing, Conversational Sales and Conversational Service into a single platform that integrates chat, email and video and powers personalized experiences with artificial intelligence (AI) at all stages of the customer journey. More than 5,000 customers use Drift to deliver a more enjoyable and more human buying experience that builds trust and accelerates revenue.


Salesloft helps sales teams drive more revenue with the only complete Sales Engagement platform available in the market. Salesloft is the one place for sellers and managers to go to execute all their digital selling tasks, communicate with buyers, understand what to do next, forecast with accuracy, and get the coaching and insights they need to win more deals. Thousands of the world’s most successful sales teams, like those at Google, 3M, IBM, Shopify, Square, and Cisco, drive more revenue with Salesloft.


Shift Paradigm unleashes the power of insights, enabled by data fluidity and creative go-to-market strategies to accelerate revenue and drive market growth. With 200+ employees in North America, Shift Paradigm is aligning sales and marketing in organizations around the world, digitally transforming customer experiences in the B2B and B2C spaces.

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Selling SaaS: How to Strategically Sell B2B SaaS

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