Q&A with Siobhan O’Reilly, Head of UK Sales at Dropbox

By March 19, 2018 ScaleUp

Q&A with Siobhan O’Reilly, Head of UK Sales at Dropbox

#Topic: Scaling SaaS Sales

4 Components of SaaS

1. Hiring

– Identify the hiring traits for your sales organisation early on

– Readjust and re-evaluate hiring process constantly as the company continues to scale and grow

– Look for applicable attributes like resilience and tenacity

2. Science of the Sell

– Identify your Key Performance Indicators and manage towards these weekly

– Review KPI’s from a global perspective and make sure it has uniformity

3. Coaching

– Importance of Coaching


· Goal

· Reality

· Options

· Way Forward

4. Culture

– Focus on Culture

  • Get feedback “ Good Leaders encourage and ask for feedback”

Key Question 1

What is the best advise that you can give for a company who wants to hire a senior sales executive that will handle and start a sales team?

In terms of profile, tenure is a useful guideline. Then consider testing for their understanding on how they see the sales methodology for themselves because if this was someone new who is starting in the company and you don’t have any sales methodology for them to follow, it would create problems for you. You need someone who is able to articulate sales targets, sales pitches, and your main value proposition. Experience in startups is also important. Very often when you hire sales people who came from larger companies, they’re used to working in an environment with rigid processes and a lot of resources available to them. A shift into a startup environment will come as a shock to them. So these are the things to be considered when you’re looking to hire a sales person.

Do you have any advise on how a startup company should put a price on their products as they move to a SaaS approach and still be competitive?

I would recommend that you read a book by A.G. Lafley “Playing to Win: How Strategy Really Works” as we spent some time in the organization talking about where we want to play and where we don’t. It’s a basic starting point in terms of where you’re trying to position your pricing model. In terms of pricing, looking at competitors is a good place to start. I suggest that you should be agile on this as it will be a bit of a trial and error. Keep track of the measurable’s like what conversions and feedback are you getting in terms of the pricing.

Key Question 2

Have you worked with OKR (Objective and Key Results) and is it something that your organization have in place?

Yes, I’ve worked with OKRs and we do this in our organization set in monthly’s, quarterly’s and annually’s. Using OKRs lets you see that you set your objectives at the start to certain period and have measurable outputs so you can measure how you performed against those objectives. So as a company or as a smaller team, you might want to sit down and decide what objectives that you’re looking to set in place, what are the key results coming from that, then that follows some kind of a workflow. Once we have the company’s goals and OKRs set, then we get each individual’s across the organization to set their own OKRs that are aligned with the company’s OKRs. It helps to drive the company’s own OKRs if the individuals have their own OKRs as well. Having it in a timely manner and checking your OKRs is important too. If you want them to be effective, you need to work them into a habit or a methodology. Some other tips when it comes to OKRs is try to look at a wide variety of topics like results, talent, and personal OKRs.

What is the ideal number of OKRs that you can suggest to set up an individual’s OKRs?

We have ranked five; results, talents, personal OKRs, upscaling, other variables and within this categories there are sub-categories which have about five to ten OKR’s in them.

Can you recommend a book that is a good read on the topic we have now?

Radical Candor is a good read. It’s based on a form of giving feedback. It coaches people on how to give feedback directly while also balancing it with empathy.

Key Question 3

Have you faced a similar situation where you shifted towards product sales from doing the services side and what have you done about it?

My organization works with channel sales frequently and we sell through the channel as well as direct sales. Some of our partners are viewing more towards product sales only and losing the professional service side of the company. The advice I can give you is to understand. If you’re removing the professional services piece, you need to understand where the support is coming from. If you are migrating or transitioning, it’s easy to underestimate the workout in transition. In terms of the product, what I’d do is emphasize what I mentioned earlier in the range of KPIs. Setting the KPIs in the beginning but also managing towards them. I think a lot of companies make the mistake of setting KPIs in place but forget to manage them. If you’re not managing towards them, there is no point in having them. They’re useful even if you’re hitting numbers and if you are growing so it’s really important that you track that information.

Key Question 4

Do you have any examples of what OKRs to use in the sales department and marketing department as well?

I would work my way into the funnel. So if you imagine your basic sales funnel of where you get your leads from, your number one OKR will be your money bank, however you measure that. Working back from that will be a good setting for OKRs. For example in your pipeline, how much sales are you generating? How many opportunities are you creating for yourself in sales? How many companies do you want to get in front of. There are so many variables so it will depend on your sales methodology. In marketing, how many leads would you expect to see in a given week or month is useful.

Key Question 5

How does your sales organization from different geographies work together?

Since I work in a big organization with multiple offices in different geographies, we structure our sales department in a way that each team can support each other in their own geography and also across the whole organization. In terms of the people working in the department, we have business development reps or sales development reps and they would generate the leads for us. Then we have our marketing team consisting of product marketing reps and sales marketing reps. We have solutions architects that are really important to us given our products are quite a technical sell. Then we have our technical deployment team and value managers. These are the people in our sales organization. I think as you’re growing the business, probably the next useful resource is the business development rep that helps support and generate the leads for the account executive to close.

Key Question 6

How do you structure your teams to sort out the different segments?

Our structure is threefold and we readjust them as we go. We have an SMB who looked at the smaller teams, Then another set of teams divided into two teams, the industry teams who are focused on selling in a specific industry, the other team sells to basically everything else.

Do you have experience in dealing with enterprise sells? What would you recommend to scaleups who are in the same situation?

My team in my organization is actually focused on doing enterprise sells. We do a lot of high velocity clients as well. In my previous work, it was also the same. It’s tempting to go after the big whales but from what I’ve seen and from my experience, the work in the high velocity deals is a good place to start. It gives you a good insight to where you would win. You can start keeping track of patterns easier.

Some tips I could recommend that would be useful is that when you’re going through this discovery stage and you’re trying to understand if there’s a fit in your company, ask yourself “what is driving this?” and “what are the drivers of the project?”. Finding the initiative internally is always important. Align yourself with the right people and making sure you’re not dealing with people who aren’t the decision makers.

Key Question 7

How do you cooperate with the recruitment team when hiring your sales team?

It depends on the size and scale of the organization. For larger organizations, have weekly meetings with your recruitment coordinator and let them know what roles you’re looking for in a candidate. Prior to hiring, do a kick off meeting with whoever is on the interview panel, discuss what you’re looking for in a candidate. That’s our standard process in my organization when it comes to recruiting.