Lesson 4

Selecting sales tech

In the 1992 film Glengarry Glen Ross, the salespeople only had two tools: a phone and a Buick. And they still sold things.

What you'll learn in this lesson...

How to evaluate sales software
The value of standardization
What software solves what problem

People have always sold things. It’s only in the past few decades that the sales and marketing tech vendors have flooded the market with dozens of systems that are considered “must-have.” Do not buy it. Be your team’s tech skeptic because even great systems often fail to solve the problem they were purchased to fix, and they’re far more difficult to remove than they are to add.

Resist shiny object syndrome in yourself and others. Keep your tech stack lean and tight. Build for a great prospect experience, but keep it minimal.

In this chapter, we’ll explain when and how to evaluate software, which types are must-haves, and why standardization is often worth a less good user experience. Like the Glengarry reps, your team will survive, and maybe even be stronger for it.

For the sales org is a-changin’.

Identify problems irrespective of tech. Use tech to solve them

People often purchase software to solve what is actually a people or process problem. Why? It’s easier than confrontation. Nobody wants to have that difficult conversation with peers in other departments. So, they invest in software and that software doesn’t perform because … it’ll only work once they earn the participation from those teams they tried to bypass. It was always a people and process problem.

Before purchasing anything, ask yourself: Am I certain that the problem couldn’t be more effectively solved by addressing people and process?

If you throw tech at a problem it’s not going to solve the problem. There’s an organizational structure component you have to figure out first.

Do you really understand the problem?

Even if you’ve identified a problem that technology really can solve, solve it on paper before you buy tech. If you can’t explain how it’ll work on a whiteboard, you don’t understand it yet. Do not assume things will turn out better than expected, and the very worst place to figure out those unknown details is after you’ve convinced the organization to spend money and it’s already cost you political capital.

If your business systems or IT team doesn’t have an architecture review board, encourage them to create one. This is a team (in the early days, just one person) who knows more than anyone else about how your CRM, ERP, marketing automation, data, and sales automation systems work and integrate. Have them review all new additions or upgrades. You’ll go slow now, but it’ll speed you up later.

“It’s like the Steve Jobs quote: Start with the customer experience and work back towards technology. You have to ask, what are you actually trying to do? A new software can look and sound great but if it doesn’t fit into your overall business strategy, it’s not only unhelpful—it actually hurts.”

Mollie Bodensteiner
, Global Revenue Operations Leader at Deel
“Every audience has its quirks. A calendar and call scheduling software everyone recommended didn’t work at a past company because our audience was farmers. [Actual farmers.] Those people were just not going to book a demo online. Good tool. Not for our audience.”

Mollie Bodensteiner
, Global Revenue Operations Leader at Deel
“When I was at Apttus, I had the opportunity to support an implementation for two customers who were competitors in the exact same space. One project was a huge success and the other a dismal failure. The key difference was the successful one had a really good architecture team. They understood the business and the technology equally well. The other company didn’t have that, was never able to use that technology to fix their problems, and the implementation was a disaster.”

Sudhakar Jukanti
, Director of Business Systems at Confluent
“An architecture review board helps you standardize. For example, if one team is using Asana and the other Jira, how do you standardize that? One isn’t better than the other, but now you have two teams speaking two languages and they’re going to collaborate less. Maybe two tools is the best option. But how will you know? The review board can find out, and validate basic things like whether it’s compliant or that one’s support really sucks.”

Sudhakar Jukanti
, Director of Business Systems at Confluent

Every system needs an owner

Never purchase a system of even moderate complexity without a dedicated owner. It doesn’t have to be their full-time job, but they do need to be the point person for answers and updates on it. If you think you have an exception to this rule, think again. Unowned systems degrade without fail, and nearly always fail to solve the problem.

“I’ve never seen a system work well without clear ownership.”

Andy Mowat
, CEO and Co-Founder at Gated
“During the evaluation, everyone will do all this agreeing. Be the lone person to say, ‘Okay but who’s actually going to do it? Who can others call when this doesn’t work? Is there a learning and development person dedicated to this, or is there a sales manager who’s willing to commit? Because if you don’t have them, and if they don’t have time, it will go sideways.”

Mollie Bodensteiner
, Global Revenue Operations Leader at Deel

Buy for 2-5 years out

When you’re growing quickly and can envision needing automation, controls, and reporting, buy the bigger tool. Go with Salesforce or Microsoft Dynamics. Not every startup can afford it, but neither can a fast-growing startup afford the painful migration off of, say, Pipedrive or Zoho, during a crucial quarter.

Mollie’s rubric—Buy the more advanced tool if you will:

  • Need scalable automation (closed deal alerts, send an email, auto-reassign)
  • Have multiple products with different sales journeys
  • Have a complex sales team structure
  • Need to force validation rules (which restrict a salesperson from submitting a deal if they haven’t completed certain fields)
  • Need to report on stages of the sales cycle (time and stage SLA infractions)
  • Need campaign tracking and attribution
  • Need a single source of data truth
  • It isn’t just a point solution and will grow with your business and technology stack
“The CRM is really a tool for your customers. Or it should be. If you’re a customer-centric business, it is. That’s what’ll inspire you to do things like auto-create renewals. When someone closes a deal on a 12-month sales cycle, create that renewal opportunity right there. Set alerts so that rep will reach out early, and the customer doesn’t feel they only call them during renewal.”

Mollie Bodensteiner
, Global Revenue Operations Leader at Deel

A starter sales stack

Every business is different. But most will end up with a common foundation. The best way to select what you need is to identify issues you presently need to solve, and figure out what systems address that.

Potential Fix
Why does the company exist?Need one place to store customer and deal cycle data
Need to automate billing
ERP or revenue-billing tool
Need to speed up signatures
Contract management and e-signature
Need to save reps from wasting time on wrong numbers and emails
Contact and account data
Sales managers need to know what’s happening remotely so they can coach
Call recording and insights
Need everyone to know how deals get done, even as things change
Knowledge management (Spekit)
Save reps time
Email, document sharing, videoconferencing, call dialers, video recorders

Know how you’ll measure success before you buy

Every tool in your stack should be able to prove its worth, and you should always decide upfront how you’ll measure success. Take a baseline of how things are doing before the new tool, and after. After every purchase, set time on your calendar in three, six, or nine months to conduct a post-mortem that includes asking people whether they used it or found value.

How do you know it’s going to be successful? A lot of people buy things and they don’t actually define what success is. At a past company, we migrated from one payment platform to another because people felt it was the only one that could support our pricing model. So we spent all this time implementing the tool and once we did …the business changed its pricing model.”

Mollie Bodensteiner, Global Revenue Operations Leader at Deel

If it’s not supporting your processes, time to upgrade

It’s important to resist adding needless technology, but it’s also important not to suffer with too little of it. If a lack of something makes your managers and their reps unhappy on a daily basis—if it holds them back from selling more—run a test and see if the fix pays for itself. Just be careful to advise that it’s only a limited test, with an expiration date. Otherwise, it’ll become difficult to rip out, even if you can’t prove whether or not it’s working.

“If it’s not working for your process, that’s an indicator that it is not the right tool.”

Mollie Bodensteiner
, Global Revenue Operations Leader at Deel

Relentlessly standardize across geos

Generally speaking, the more exceptions you make in how you deploy or configure tools, the more maintenance there will be later on. It’ll also be incrementally more difficult to onboard reps.

After all, every software acts like a living thing. Each vendor’s product team is constantly updating and improving it, and at the same time, you’ll be updating the way it’s configured for your team. For example, you’ll be altering objects, workflows, buttons, and rules in Salesforce. The sum of all those changes is a progressive tax on your sales team’s time.

“The more exceptions you have in the process, the more custom logic you’ll need to compensate. Customization makes things more difficult to learn—think about the new learners—and it’ll be exponentially more difficult to make each successive change to that system.”

Sudhakar Jukanti
, Director of Business Systems at Confluent

Your greatest tech challenge is convincing people to think ahead

Recall back to Lesson 3 where we talked about how everyone thinks on different time horizons. Sales managers and account executives think in terms of deal cycles and quarters. Their requests will invariably tend to be short-sighted, and they’ll expect immediate change. But you need a cohesive plan, and to scope proposed changes with the review board. You want to make friends, but you can’t say yes to everything, otherwise, your tech stack will evolve into an unmanageable mess.

“Think ahead, but also try to encourage others to think ahead. How can we all escape the trap of constantly trailing? Of always having a backlog we’re never catching up on? How can people imagine the problems they’ll face tomorrow, so you’re addressing things that have yet to come? Most teams are always trailing. How do you not trail?”

Mollie Bodensteiner
, Global Revenue Operations Leader at Deel

Never buy the roadmap

Final word of advice: You can buy into the vision of where a tool is headed, but do not, under any circumstances, buy something because you are promised features. They will never come as fast as you need them, if they come at all.


You’ve finished Lesson 4: Selecting Sales Tech.
Lesson 1
Lesson 2
Lesson 3
Lesson 4
Lesson 5
Lesson 6
Lesson 7
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