Liberate Sales Reps and Customers with B2B Sales Automation


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Agile monetization expert Jim Gearhart joins us in this Q&A to share his thoughts about what B2B technology companies should think about when enabling sales automation and customer self-service versus directing sales motions through human salespeople.


Doug: Jim, you have such an interesting background having been an IT leader responsible for implementing and managing agile monetization and sales automation at companies like Zendesk, Atos Unify and Omniture. For B2B companies, when does it make sense to implement customer self-service vs using reps?
Jim: I think the objective of any company should be to provide as many self-service options as possible to customers. At Zendesk, as a born-in-the-cloud company, we excelled early on at enabling customer self-service and we exceeded $100m in ARR business before contemplating hiring sales reps. However, ecommerce only gets you so far, particularly as you move up market at the enterprise level. A certain segment of customers wants to transact and will accept the offerings that you have online, and you try to enable this to the fullest extent possible. Exceptions might exist when a customer’s procurement practices, security, or legal processes preclude the ability to transact online.  But in many cases B2B buyers prefer self-service, and for your smaller customers, self-service is the only cost-of-sales optimized approach.

Doug: For companies looking to migrate existing offline customers to an automated sales process, what are some key considerations you’d highlight?
Jim: #1. Align with Sales & Other Stakeholders. Establishing an aligned approach with all of your internal stakeholders is key. Human and automated selling both play critical roles and they can work together towards a common goal.

#2. Segmentation. You need to segment your customers by size, products used, or other criteria to ensure you have a defined set of customers you can address at scale through automated processes. Customer self-service can be essential for low cost and frictionless acquisition of your SMB and mid mid-market customers; and it plays an important role as well to free up sales rep time from low value transactions and administrative tasks, such as adding a few seats to an existing subscription.

#3. Standardization & Disclipline. Consider the buyer’s experience, to reduce as much friction as possible in both the initial transaction and subsequent cycles. Go the way of In-N-Out Burger: offer very standardized and limited options with only narrow exceptions permitted. You have to put in place programmatic controls to protect your standardization. Once sales reps are involved there will be human temptation to make special exceptions to avoid losing any sales. Some organizations end up with something like 80% of their deals being non-standard and these exceptions can create a huge internal overhead on an organization in service delivery and account management. The goal should be to strike a balance between revenue optimization & customer experience. Shifting things to self-service can be a gradual ongoing process at which you keep chipping away but you should strive to have a framework in place from the onset.

#4. Off Ramps from Self-Service. While self-service may be the only option you offer to your smallest customers, as you move up to your mid-market and enterprise accounts it becomes increasingly important to provide off ramps that allow customers to speak with a rep when needed.

#5. Cost Benefit Analysis. It really becomes a cost benefit analysis in terms of selling online vs through reps. If at some point you’re selling offerings into certain target segments that require additional levels of customer engagement and negotiation, your company has to decide how important that piece of business has to be. You may want to consider asking yourself, “How do we provide volume pricing and bespoke services through self-service?”

Doug: That’s an interesting point you make about the ongoing tension between contract standardization and customization. Could you share a bit more about this?
Jim: You want to avoid a situation in which once a customer is acquired through a sales rep, every subsequent change to that customer’s contract requires ongoing sales rep or other internal efforts. To achieve this you must be rigorous in ensuring deal standardization, particularly for small opportunities. To avoid turning away business, many organizations fall into a trap of allowing sales reps to get creative on small deals in ways that simply are not sustainable from an operational perspective. You could have, for example, a case where you’d spend thousands of dollars of internal work for a couple hundred dollars of additional revenue. You have to be intentional about the types of businesses and types of deals you’re pursuing, and how supportable these deals are through self-service and/or other things like renewals, expansion/contraction, and entitlement tracking. You want to avoid spreadsheet exercises for all of these one-off deals by standardizing and automating.

A customer might be spending a total of $5k annually and constantly expanding/contracting. In a manual process, while the revenue looks good there is so much back and forth that the operational overhead costs more than the revenue. The “hair ball” gets messier because as you put the customer into self-service you fear that you’re missing out on the up sell/cross sell opportunities because you’re no longer having those customer conversations. This is where telemetry becomes essential. Having a way to programmatically raise flags if a customer is at risk for churn or if there are indications the customer is ready to buy more seats (e.g., high use) or additional products/services. You don’t know which of your customers that start small will then expand to be monster accounts.

Doug: What are examples of scenarios where a self-service customer might want “off ramps” to purchase from a sales rep?
Jim: The customer may have multiple concerns in areas such as legal and security. A lot of times larger companies – even if making a small initial SaaS purchase — will have a lot of red tape (g., Safe Harbor Agreement, purchase orders, special discounting).

As a customer’s buying commitments increase it’s likely that they will seek more negotiation flexibility whether it be price, support or other terms.

Doug: In your experience, how do your sales reps react when you expanded sales automation and customer self-service?
Jim: Often sales reps love moving things to ecommerce and self-service. It removes busy work and can be done in a way that doesn’t negatively impact their overall compensation.


Doug: What is the trend in regards to who “owns” customer self-service?
Jim: The trend is definitely seems to be shared ownership between sales & marketing teams that cater to customers/deals on the lower end of ACV.  You want to attract, nurture, and close these deals at high volumes, with low friction.

Doug: What’s a typical go-to-market segmentation one might see for vendors using both customer self-service and human reps?
Jim: Customer segmentation might be based on variables such as the number of employees, initial deal size, lifetime customer value (LCV), and software level, and fall into two or three buckets like:

  • High Velocity/SMB.Typically fully automated other than for cases where the customer raises their hand or you looked at the data (e.g., growing account) and intervene with a rep.
  • Corporate/Mid-Pooled or assigned accounts where human involvement is often still high, but vendors are increasingly moving to a hybrid approach that combines self-service and human reps.
  • This segment typically has at least one dedicated rep to an account, and use of self-service is less prevalent, but should still be a goal if appropriate and feasible.

Doug: For B2B vendors that implement customer self-service storefronts for their SMB customers, what’s next?
Jim: Ultimately, you want an omni-channel approach. Today’s customer is expecting instant gratification, and you have to deliver that – and make it easy. It’s all about customer experience. I think of other companies that I’ve done business with and a lot of times it’s a speed thing. If you fill out a web form and 1.5 minutes later you get a call from a rep, that’s a home run. Some other areas I’d highlight:

  • Renewals – Implement any automation you can within the sales process.
  • CPQ – Make your self-rep and customer self-service CPQ processes as fluid as possible.
  • Telemetry – The really big opportunity is getting into the data and having strong instrumentation in the products. Having strong signals that you can use to automate customer engagement and the transaction is a game changer

Doug: A lot of vendors talk about expanding their ability to capture customer telemetry. What kind of transformation could this enable?
Jim: Here’s an interesting thing to contemplate as an example: with your typical piece of consumer electronics the consumer only uses about 15% of the device’s features or only recognizes about 15% of the device’s potential value. How much of the value remains unlocked and could make the product stickier? For example, show me (as the customer) the 5 things I need to do to maximize the value of the product. LinkedIn does a good job of this with the LinkedIn profile score. As the vendor you might show the customer’s progress against maximizing the value they can get out of your product based on carefully considered and specific actions within the product.  And as the vendor you’d want to monitor signals for opportunities to intervene to prevent churn, like a drop off in specific use cases by the customer or an increase in the number of unpleasant customer interactions with sales & support.

Doug: Seems like every vendor selling subscriptions these days understandably aspires to achieving a 360 degree view of their customers to facilitate the best possible customer experience and to ensure ongoing renewals. What are some ways companies achieve this?
Jim: A common approach is to create a data lake that draws customer information from various systems such as those supporting sales, support, and product telemetry. And tying an analytics platform to your data lake enables actionable insights through composite signals curated by data science.

About Jim 
Jim Gearhart is a business-minded tech executive with extensive experience in developing & executing IT strategy, building high performing teams, and delivering results to maximize business outcomes. Jim was Senior Director, Enterprise Business Applications & Development, at Zendesk where a major focus of his was agile monetization technologies and systems. Jim has served in various IT leadership roles at Atos Unify, Omniture, and Wells Fargo. Find Jim on LinkedIn.