Innovation Blog

How Much Should We Rethink the Sales Process During COVID-19? Advice from Stack for Startups Trying to Sell


A guest post by Scott Jenkins, CEO and Founder of Stack, a MassChallenge FinTech partner

Over the past half-decade, the majority of my professional life has been dedicated to helping early-stage companies find a scalable path to growth. Whether directly with startups, or through collaborating with VC and Accelerator partners, the goal has always been to take the expertise and sales process that lives inside a founder’s head and extract it in a definable, documentable and organized way so that company stakeholders can understand and adopt these best practices. Most of the conversations in the past 5+ years have been about growing, scaling and running fast. Inevitably, the tone has shifted in the last few months.

Regardless of the industry you’re in, or the position you hold in your company, we all are going through some very tough stuff. As we all are trying to settle into the new normal, many startup founders’ thoughts undoubtedly turn towards how to continue the upward trajectory of revenue, even with the hurdles and headwinds that COVID-19 presents. From our experience working with fintech companies, here are 5 practical items we at Stack believe are useful when confronting the daunting task of selling in today’s environment.

1. Most of the fundamentals of selling continue to be the same.

While the “rules” of selling into enterprises are shifting, the “game” itself remains fairly consistent:

  • Identify your ideal prospect
  • Understand what their priorities are
  • Determine together if your product/solution can help them advance their priorities
  • Decide together the economic parameters of the deal
  • Move forward, or move on

You have been doing this since you started your business, and your team has developed the appropriate skills and processes to effectively sell using some version of that sales cycle. This is a good thing! You do not need to reinvent the wheel. You can, however, make adjustments based on your analysis of your approach and the market, which you should do regularly in any environment – not just now.

2. Be the partner that is focused on the short-term priorities of your prospects.

In the span of weeks, companies have gone from hockey-stick growth projections to lowering their headcount. Now is not the time to be thinking about long-term deals. This is the time to be helping your clients survive in the immediate term. Get to the heart of how the following have been affected by the pandemic:

  • Company priorities
  • Division priorities
  • The decision-maker’s priorities
  • Budget
  • Decision-making processes

Once you have a better idea of their new worlds, it will be much easier to propose an offering and solution to address the acute problems they are facing — and that are likely keeping them up at night. Being a startup can be a huge advantage here. Be nimble and responsive, and meet your prospect where they are currently.

“We’ve really focused on the key pain points we’re hearing the last couple of months from our clients, have tightened our offering, resulting in a key client acquisition in April.”

-Marc Miller, Co-founder, CEO, WalletFi

3. A suboptimal deal now is usually better than no deal at all.

Now, a deal that you wouldn’t have considered three months ago may be the foot in the door you need.  When the world begins to be restored to some semblance of order, clients will remember those partners and vendors that were willing to be creative and flexible during difficult times, positioning you to have deeper and longer-term discussions down the road.

Now is the time to figure out how to simplify your offering and be the partner or vendor that does the heavy lifting. In this environment, anything that feels complicated or time-consuming will likely get shelved for now. This includes your deal. So when considering what offering to present, revisit the basics of building product and come up with the offering MVP. Slimming down the offering and laying out the sales and implementation process will help guide the conversation with your prospect and lead to a quicker decision of whether it makes sense to move forward at this time.

The goal isn’t to take any deal at any cost, but it is more to be as open, flexible and creative as possible to keep traction and momentum moving in the right direction. By continuing to add to your client count and top-line goals, you’re also positively impacting your company in a number of different ways, including sending positive signals to investors (current and potential), employees, and prospective partners.

4. Being the one to bring up ‘now may not be the right time to do business’ can actually help you.

There have been many conversations recently about striking the right tone between persistence and passivity when diligently following up with prospects. You want to be empathic and understanding, yet also need to work a prospect through a sales process and pipeline.

If you find yourself continuing to send passive, “just checking in” emails, consider being prescriptive, direct, and empathetic in your wording. Acknowledge that wherever you were in the sales process, things likely have changed. Throw out a few specific ways you could move forward, and consider whether the prospect has a priority or problem that you can address now. If the priorities are less clear, consider asking to schedule a meeting 4-6 weeks out in order to maintain momentum. If the prospect is simply swamped, table the discussion for a few months, but let them know you may occasionally send them an article, thought, or suggestion if you think it’s applicable.

Many times in sales, you don’t want to give someone ‘an out’ by suggesting an alternative other than moving forward quickly. In this environment, however, when many people aren’t sure how to prioritize things, they may appreciate a ‘soft out.’ By setting a check-in farther down the line, you’ll likely have a grateful prospect when you do resume discussions.

With the world seemingly turned on its head, you have the opportunity to actually check in on the people behind the sale. How are they holding up? How are their families? Can you do anything to help them? People enjoy doing business with people with whom they have a connection. Try to find that connection in an organic way. It will make the good conversations even more exciting, and the tough conversations and negotiations a bit less daunting.

“I’ve seen better engagement with FI prospects I’m working with by combining providing specific timeframes (at least 2 weeks) to connect with the person – not trying to push the next sales stage.”

-Patrick Rivenbark, Business Development Manager, Cyberwoven, Co-chair, Operating Committee – Carolina FinTech Hub

5. Double down on direct selling.

Many startups very rightly lean into channel and partner selling. It’s a good way to gain operational leverage, avoid hiring large sales forces, and reach more people with less FTEs.  However, when selling via channels, you are, by definition, a step removed from the prospect. Now is the time you want to be as close to your clients and prospects as possible, to gain a closer relationship, hear first-hand their challenges and priorities, and shift or iterate your offering quickly when needed. If your sales strategy leans heavily on channel partner selling, you may want to revisit this to ensure you’re making the most of your time and resources.

By focusing on direct selling, you can also free up bandwidth for partnership/business development team members that normally manage those channel relationships, allowing them to interact directly with prospects. This can help move the needle on short-term revenue opportunities.

“At Bridge, we have put more emphasis on the direct selling since March, and this has yielded meaningful conversations with prospects-turned-clients that wouldn’t have otherwise happened if we would have put that effort into our partnership channel.”

-Rasheed Hammouda, CEO, BridgeFT

We’ll Get Through This

This is an unprecedented time in all of our lives – no one can argue to the contrary. In my experience, it is in times of turbulence and uncertainty when entrepreneurs forge a path forward. Focus on the building blocks of selling, and approach the process with an eye towards empathy. The tactics and mindsets have shifted, but with focus, small tweaks to how you’re selling, and dedication to the fundamentals, you can set yourself up for success in the short-term and beyond.


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