10 Sales Operations Challenges and How to Overcome Them

7 min read

Sales operations is the function everyone relies on to build smooth processes, bridge the gaps between sales and other departments, and generally keep the sales machine ticking over as efficiently as possible. But with that comes challenges. Most sales operations leaders will have experienced a torrent of multiple requests all before 9am, or will have struggled to secure buy-in for an exciting new tool. Before you throw in the towel in despair, our community of sales ops leaders have shared their top 10 sales operations challenges and how they overcome them.  

Challenge #1: Inheriting legacy processes

Will Dean, Head of Operations, Persado

We had pretty patchy Salesforce usage. It wasn’t configured in a way that sales or customer success wanted to use it and it wasn’t giving them the outputs they needed. So, we basically did a complete reset, put Salesforce back to its original format, almost like it was out of the box, configured it, and streamlined it working towards a point where the inputs going into the system were correct so that we could rely on the outputs.

A really a big part of it was trying to get people to use the system (Salesforce). Believe it or not there were Google sheets floating around as a means of tracking pipeline. We pretty much did an audit to make sure we were comfortable with what we were getting out before we could start accurately leveraging the data to draw insights and recommendations for the business.

You often find that unless there’s been a clearly defined roadmap, systems such as Salesforce can evolve into something that serves a number of individual use cases but does nothing particularly well overall. Part of sales ops is ensuring that use cases don’t just help one person, but they add value to the wider business. What you tend to see when these push back and validation doesn’t happen is that the Salesforce instance turns into this monolith of a huge number of fields, plugins, page layouts, outdated reports and useless dashboards. People just don’t want to go in there as it has become such a mess.

It is tricky, you have to be a little bit patient and slowly get people bought in with some of the outputs. I think when people started to see that we were tracking the right things and were giving them value, then they got the whole simplification piece.

We were pretty militant when enforcing usage, looking at how many people logged in and how often, making sure they were updating their opportunities and pipeline on a timely basis. It’s not first nature and it’s not the nicest tool to use at times but we’ve leveraged some third-party tools to facilitate adoption.

Challenge #2: Working with an ever-evolving product

Gilles de Clercq, Business Operations Analyst, Showpad

Since we are in software, we are ever evolving. I think we have three or four releases per year. So the message we bring to our prospects and clients is evolving every three to six months. In order to do so, this requires a lot from both our back end in terms of product engineering but also the GTM team since the message we bring has to be unified from the top of the funnel to securing the sales contract. To give you an example, we’ve introduced over 20 features over the last six months, so we need to know which feature every individual client is using. It’s very interesting but also very demanding for the sales teams, the customer success teams, legal, finance and so on. When you change your offering that much, it demands a lot. But it’s also interesting.

Challenge #3: Onboarding

Catherine Mandungu, Director of Sales Operations, Ometria

I was involved in the phase two roll out of a particular sales technology. The reason it failed was because no one had consulted sales on what the processes currently were and what they needed. I picked the project up at the onboarding stage and training what was actually implemented was hard because I got a lot of feedback saying it didn’t meet the salespeople’s needs.

I learnt from that experience that you need a lot of involvement from people on the ground. I decided the first thing I would do would be to sit with everyone in the business to understand how they work and what processes they use. I could then see where the consistencies and inconsistencies in the processes were. It was all about analysing how those individuals worked and how I could bring their working styles together. I then presented my findings to the team before I made any changes. This resulted in people getting excited about implementing something new because they were involved in the discussion.

Challenge #4: Juggling ad hoc requests

Michael Newton, Sales Operations and Data Analysis Manager, Perkbox

The danger with a sales ops role is that people sometimes ask for help with every little detail, for example why they can’t see something in a particular report. So it can be hard to prioritise your time.

We’ve tried various processes to deal with this. One process we’re using at the moment is a Slack channel for sales ops. We also found that when a lot of people have an issue they would speak to me, marketing ops, and our Salesforce admin about the same issue. It wasn’t very efficient. The Slack channel encourages more openness and visibility between the teams.

Challenge #5: The marketing and sales alignment

Cris Santos, Director, EMEA & LATAM Sales Strategy & Operations, Docusign

Seeing sales and marketing as two separate departments is the first mistake. For me, marketing creates the demand for sales. Sales can’t exist without marketing and vice versa. Having that broken relationship is very common in companies. At DocuSign, we removed that wall across the two organisations and we got the marketing and sales leaders together to discuss targets. And we concluded that there is no such thing as a separate sales target and a marketing target. I think it’s that lack of accountability that can create that tension between marketing and sales. So we put together a new measurement on the compensation plan to align both departments. 

At the end of the day, organisations are made of people, so we need to make sure we get those people together. We have the marketing team spread across different countries so they’re not sitting here with the main sales team, but we go and see them all the time, they come to see us, and we have regular contact over the phone. I think that explains a lot of the success here at DocuSign; people are very open to dialogue and willing to cooperate in a holistic way.

We make sure we have the right systems and processes in place to be as efficient and fast as possible. One of the first things we did was to reassess the lead scoring system and we worked with marketing on that to make sure that we are focusing our time on the best leads. However, even if they’re not an MQL, we continuously monitor them and we’ve invested a lot in a sales development organisation that helps with that machine. We have people in charge of processing those leads so we’re on top of everything that’s coming in. We have inbound reps and then we have the outbound team. We’ve created a sizable sales development organisation, similar to what Salesforce, for example, have created.

Challenge #6: The sales enablement and sales operations alignment

Brandon Bussey, Director of Revenue Operations, Lucid

At Lucid we were restarting our enablement team when I joined. We brought in someone to run and build that function out and we moved the function into sales ops. It’s been beneficial in making sure both teams are aligned and that we’re partnering on our initiatives. It also helps enablement to focus on where they’re driving metrics and what metrics they should be focusing on.

We have our regular team meetings, which results in good osmosis. But I think the water cooler effect is where the best interactions happen between the team. That’s what our current Head of Enablement is great at. She’ll hear someone talking in the background and she’ll ask to listen in, give her feedback and share ideas. It drives a more cohesive team and a more go-to-market approach to the sales floor. One area we are now pushing is to also have our enablement team out with the sales floor more for that same reason.

Challenge #7: Alignment difficulties when teams are spread out geographically

Justin Kersey, VP of Sales, UK, Merrill Corporation

It’s about having a greater understanding of what the end objective is or whether it’s tools or processes. Then you can assess whether you need to deconstruct it and rebuild it based on local needs. Largely, we take a lot of what our North American counterparts put together, but it’s trying to make sure that we have a voice. Again, we have a more nuanced sell here, so we remind them on a regular basis that there are certain components that we’re going to have to modify as we deploy new tools and processes.

Before any tools or processes are deployed, we need to make sure we have a seat at the table and we’re involved in those discussions to represent EMEA more effectively because certainly in the early days, we were deploying things out the door and it wasn’t working for us.

Challenge #8: Securing buy-in for new initiatives

Jay Khiroya, Head of Operations, Doctify

No matter how amazing the process, it will always fail if you don’t have the buy-in from those that will be executing it on a daily basis. Always analyse the impact the rollout will have, and to whom. The only way this will be successful is getting the buy-in and highlighting the key improvements this will bring to the team, function and organisation – in the short and long term.

Challenge #9: Reaching long-term company goals while satisfying immediate needs

Cornelia Klose, Global Sales Operations Manager, Mailjet

There is a slight difference between being solution-driven and outcome-focused. During my early years in Sales Ops, I often tried to find a solution for a problem, and I was often very successful… Until I realised I wasn’t fulfilling the overall purpose of Sales Operations. That is to say, I wasn’t focusing on the outcome. Don’t get me wrong, being solution-driven is a key strength for Sales Ops. But finding a solution only brings half the joy if it doesn’t fit within the company’s goal. That’s why understanding these objectives and implementing them in each solution is one of the key skills of a good Sales Operations Leader.

Challenge #10: Keeping up to date with the latest sales technology and finding the right tools

Cornelia Klose, Global Sales Operations Manager, Mailjet

What are the right tools? Sorry to disappoint if you’ve heard this one before, but it really does depend. Does your Sales team need, for example, a digital signature tool to send quotes to clients? Or a marketing automation tool for their outbound activity?

The role of Sales Operations is to choose and manage the right services.

See what’s out there, stay up to date with the latest tools and regularly review which of your tools might have become obsolete in your toolkit.

Here’s a list of questions to ask in all sales tool demos:

  • Can it improve the sales process or will it add an additional step?
  • Can it be integrated seamlessly with the other sales enablement tools? If not, how much manual work will it add to the sales process?
  • At what step of the sales process should the tool be integrated? Can it replace one step?
  • Can I calculate the ROI of the tool directly after its implementation or is it just a nice gadget to have?
  • Oh, yes. And, how much?!

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