Interview with Will Dean, Global Head of Sales Operations at Persado

I came over all autumnal as I made my way through the Victoria Gardens towards Embankment café. Browning leaves gently made their way to the footpath below, occasionally being thrown off course by the cool Thames breeze. I was about to meet Will Dean, Global Head of Sales Operations at Persado.

Will started life at Deloitte, making his way into financial planning and flirting with some of the many disciplines of sales ops, before taking on a fully-fledged sales ops role at Persado. We planted ourselves outside, armed with a strong americano to get the cogs moving.

Rory Brown (RB) – So Will, first things first. Financial planning at Deloitte to Sales Ops. How did you make the move?

Will Dean (WD) – Well, during my time at Deloitte I’d worked on a number of M&A transactions involving high growth technology businesses. I was keen to move in house and see things from the other side whilst still retaining a commercial focus. My first move was into a company called Ooyala, a SaaS business that had rapidly grown through acquisition since its formation. I took an FP&A role there, which beyond your typical financial analysis, involved closely supporting the regional sales team and general management. Naturally this meant adopting a very commercial outlook whilst still leveraging my analytical skills and knowledge of finance, particularly in relation to forecasting and revenue modelling.

Following Ooyala I had a chance to lead the Sales Ops function at Persado and build out a team from scratch, which is what has brought me to where I am today.

RB – What sort of size is Persado?

WD – We’re about 250 people globally, with about 80 in the commercial organisation across business development, pre-sales, sales and customer success.

RB – Were you the first Sales Ops person to come in?

WD – We’d had some team members that provided sales ops support in the past but it was never really recognised as a separate team. I was the first to establish a team here and build out a proper function to support and drive the business. It’s been interesting and challenging to come into a situation where there wasn’t a previous dedicated function - quite often it’s about unpicking the historical footprint in Salesforce to help understand the wider picture whilst cross referencing this with people in the business.

RB – When you talk about revenue modelling, what does this mean exactly?

WD – It’s all about building out an accurate projection of the business' revenue based on a clearly defined set of assumptions. At Ooyala, the recent acquisitions meant the business sold a combination of products all packaged up and sold differently, be it through subscriptions, perpetual licenses or on a consumption basis. A lot of the revenue modelling involved building out and challenging the assumptions and inputs, in particular working with the sales team to understand the pipeline and its maturity, the product mix of opportunities, conversion rates and seasonality amongst a number of other things in order to build out a revenue projection over a specific time frame.

Obviously with all projections and forecasts, the further out you get, the more speculative and harder it becomes to accurately depict what is likely to happen!

RB – To you, having been in sales ops for a couple of years now, and a little bit prior, what are the core disciplines of the sales ops function?

WD – It’s a mixed bag. I think previously sales ops used to operate in isolation as a support function to sales. It still very much is that but I have multiple stakeholders now across sales, finance, product, HR and marketing. It’s pretty much the full sales cycle from first campaign to signing and everyone that touches in between.

RB – What about customer success?

WD – Yeah, absolutely. It all ties up, making sure we are managing our ongoing book of business and ensuring people are appropriately incentivised on this front is a core part of the role. There’s both a strategic and operational element to this, in terms of coming up with the right incentive structure and then delivering on both this and the associated reporting to ensure we are continuously benchmarking ourselves against industry standards.

RB – So you’re doing all the comms plans, too?

WD – Yes both in terms of the strategic direction and operational execution. It’s quite a big task so it’s almost like I’m doing three roles in one at times.

RB – So, you came in and you inherited a few legacy processes. What were the first things you were looking to tackle in this role?

WD – Probably a bit of a health check on how things were going in the business. 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.

RB – How did you then get people on board with the unification of a process? Sounds tricky…

WD – Well, 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, 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.

RB – That’s interesting, and leads onto my next question. Outputs and people realising the fruits. What are the first outputs and bits of value you gave your users?

WD – As simple as:

1. A clear view of how much pipeline we have by team
2. What was the maturity of that pipeline by age and sales stage?
3. What is driving the pipeline changes week over week?
4. What are the pipeline conversion rates by team and rep?
5. Who’s falling behind on pipeline creation?
6. When are deals dropping out of the funnel and what are the reasons for this?
7. Why are certain opportunities getting stuck in certain sales stages?

Essentially, a single source of truth for better transparency and visibility across the business.

RB – What have you done to capture activity?

WD – This can be tricky to report on but we’ve leveraged the activity object in Salesforce to ensure all outbound activity from calls to meetings are accurately tracked, logged and reported on through the use of dashboards.

RB – And what about sales stages, ensuring they’re being used in unison?

WD – That’s one thing we’ve really focused on. Agreeing the criteria and the validation checks to ensure certain ‘must haves’ have been met before opportunities move to the next stage. To follow up on this and ensure things are flowing through the funnel correctly we do real time pipeline reviews to ensure the overriding deal commentary actively depicts the correct sales stage. It’s critical to large parts of our analysis to ensure we get the right inputs here.

RB – And are you running these reviews?

WD – Yes. We have a regional and industry focus with Sales VPs leading each of those teams. It tends to be a weekly team meeting to review the pipeline and any associated analysis to make sure they are getting the output needed and to help us better understand the pipeline and any gaps we have from our side.

RB – What’s your tech stack?

WD – Marketo from a marketing standpoint. Our Business Development teams use Outreach for their outbound and email drip campaigns.

In terms of pipeline management, we use a tool called Troops that integrates with Slack and Salesforce so that the sales team can get prompts and reminders to update their opps.

On the reporting side we have some small plugins that simplify the creation of visualforce pages which are used for a number of different purposes. We also have an integration with Dropbox for document management and have some simple integrations with some third party data providers for account enrichment and territory management.

At the tail end of the pipeline we have Docusign that we are currently in the process of implementing.

RB – This technology was mainly here before you arrived. So, if starting from scratch, how would you order your tech integrations?

WD – Oof, good question!

RB – It’s getting tough now, Will

WD – First and foremost you’ve got to get Salesforce configured the way you want it before you even consider doing any integrations. Then you’re on to your marketing platforms, outreach tools and any third party data providers to assist in territory mapping. Once you’ve got the top of funnel sorted I think you’re on to everything that influences the pipeline from qualification through to signing. This ranges from contract logging which can be done manually or through native Salesforce applications to all the other small bits in between that aid reporting and pipeline management but are not critical to a functioning Salesforce environment.

RB – Could you see sales ops being a c-level role?

WD – I see it more as a hybrid with a Chief Commercial Officer type role. I’m not sure if it will have its own place.

I think the reason it’s grown in importance is that data is so prevalent in SaaS businesses and there is so much focus on nailing the metrics in SaaS, whereas before, if we go back 10-20 years, it was more of a nascent industry and all of this stuff hadn’t been figured out - there weren’t enough data points to identify what was good and what was bad from a metrics perspective.

It’s become a lot easier for SaaS businesses to benchmark themselves with the volume of companies in the industry now. As such, investors are looking to see proof in the metrics that something is actually scalable given the right market dynamics. A lot of this stuff comes from the sales ops function.

RB – Famous Duo that depicts the relationship between a Sales Ops and VP Sales?

WD – Hmm, a tricky one. I'll go with Tom & Jerry, but without the axes, dynamite and anvils!

We’re both always busy running around and always trying to get something from one another. Whilst this can create some challenging business circumstances, at the end of the day, once all is said and done, we always end up looking out for one another and doing what’s best!

RB – That takes me back! Thanks, Will, it’s been a pleasure.

Want to get more insights from the sales ops leaders? Read our other posts in the sales ops interview series.

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