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Interview with Dave Sherry, director of Land and Expand

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How does nine year of working in SaaS sales look like? What is the most challenging part of operation in this market? Dave Sherry, Director at Land & Expand tells about his experience! He talks about the obstacles he has faced over the years and how he become director.


Could you tell us a little bit about yourself?

I’m Dave and I’ve been working in SaaS sales for the best part of 9 years now, having worked with 2 x SaaS companies before going out on my own around a year ago. The first company was a San Fran advertising technology company called AdRoll, where I joined their Dublin office as the first SDR in their first few weeks of operating in EMEA. I started as an SDR, and progressed into a commercial AE and eventually an Enterprise AE. I stayed with the company for  just under 4 years, and then joined another US company called Amplitude as their first sales hire in Europe. I worked as an enterprise account executive, before moving into a strategic account executive and then moved into the Head of business development role in early 2019. I worked at Amplitude for 3 and a half years in total, and then for the 12 months I’ve been working as a SaaS sales consultant, which has been a blast so far.



What do you think makes a great SaaS salesprofessional?

In my opinion, there are two things.

First, you need to have a natural curiosity towards the industry you’re selling into and towards types of buyer you’ll be speaking with. It needs to be an authentic and natural curiosity too, or else buyer’s will just smell bullshit right away.

The second one is consistency. What I mean by that is, you need to be consistent with your daily/weekly/quarterly input activities, in order to achieve consistent quarterly / annual output. It pays off to be predictable, because that predictability will not only help you succeed, but it’ll help people manage & coach you better.


”I think the most difficult part of being a sales professional is having to grind through the polarizing emotional gain/loss that comes with the territory of starting a career in sales.”



What, in your experience, is the most difficult part of being a sales professional?

I think the most difficult part of being a sales professional is having to grind through the polarizing emotional gain/loss that comes with the territory of starting a career in sales. For a few folks, the extreme highs and lows in sales can be energizing, but for a lot of folks it can be uncomfortable and unsettling. Most of the people who are new to sales will naturally go through this evolution in their first 0-3 years in sales, and my advice to them is include things into their life early, that will keep them centred and balanced such playing sports, working out, meditation, music, whatever. Burnout is a real thing, and it can knock you back for a few weeks/months. You might think it only happens when we overwork ourselves during the tough times, but it actually also occurs during the peak moments of the highs when we channel our inner “money never sleeps” mindset and sacrifice everything else to “get another deal in”. The best sales reps I’ve ever worked with were those who started their work at 9am, finished at 6pm, and lived their life for the evening. Learn to manage the highs and lows.



”The best sales reps I’ve ever worked with were those who started their work at 9am, finished at 6pm, and lived their life for the evening. Learn to manage the highs and lows.”



What do you think is the secret to smashing quota?

I mentioned it before, but being consistent is the not-so-secret secret.  In sales, you’re obviously given your target. That target is the output of your input. And what’s really important, especially if that target seems far away from now (e.g a quarterly target or annual target) , is to translate that output into the things you need to do on a daily or weekly basis, i.e. the inputs, in order to achieve the output. Acknowledging your inputs and organising your schedule to consistently execute these week-on-week, will take care of the outputs.


What advice could you give other sales professionals who would like to move up the ladder, who would like to get a promotion or become a manager like you did?

I and a lot of the people I’ve met working in sales originally came into the function with the expectation that hard work, achieving results and being a good person would naturally propel us up the ladder. This didn’t turnout to be the case. In the world of early stage SaaS companies, where the majority of internal processes and procedures are undefined and still getting figured out, it’s important to acknowledge that your career progression within the company – is up to you to own.

Firstly, if you have trailing 6+ months (ideally +12) of overachievement against quota in your role and you have aspirations to grow into a new role in 12 months time, it’s super important to be clear & open with your manager about this. Lay down your mark of your intentions to pursue the role, ask them if they will support you on this internally. Then, ask if there is a promotion path process internally (if not, co-create this with your manager, and HR). The promotion path should be a comprehensive document that tracks key milestones, areas of improvement and deliverables each quarter/month over a 6-12 month period.

Secondly, develop your internal brand at your company. When you’re approaching the end of the promotion path period based on the document that you and your manager have created, it will likely then lead to a discussion amongst the leadership team about your promotion. Your internal brand will be a key driver of this decision outcome and the key things that drive your internal brand are:


  • Your results against quota
  • Your growth in key areas over the trailing 12 months
  • How you adhere to the culture values/operating principles of the company on a day-to-day basis

”The breadth and depth of the emerging solutions to real business problems is mindblowing, overwhelming, but definitely exciting to follow.”



What do you like about working in the SaaS industry?

I enjoy solving problems which is one of the main reasons I got into sales in the first place and I see SaaS companies as the ultimate problem-solvers. Over the last 12 months I’ve spoken with dozens of exciting seed stage companies and very often I’ve found myself laughing to myself on calls saying “Wow, that’s a big pain these guys are solving”. The breadth and depth of the emerging solutions to real business problems is mindblowing, overwhelming, but definitely exciting to follow.

”I think that the role of sales folks will naturally gravitate into a more hybrid setup between sales & customer success, where compensation payouts will be more focused on expansion revenue instead of net new logo revenue.”



What do you think the future of sales is heading towards?

There’s a lot of noise at the moment around product-led growth, and I’m a believer that it’s going to be the next big wave. In simple terms, product lead growth is revenue growth for a business which is primarily driven through it’s self-serve product experience, and not necessarily through a sales person or an SDR calling a company and saying “Hey, you need to buy this product.” When you think of companies that have nailed product-led growth, you think of Dropbox, Atlassian and Asana (amongst many others).

And so, for salespeople, that’s kind of an interesting one. The initial thought might be “Oh my God, I’m going to be out of a job”, when in reality, I don’t think salespeople are going to be out of a job. I think that the role of sales folks will naturally gravitate into a more hybrid setup between sales & customer success, where compensation payouts will be more focused on expansion revenue instead of net new logo revenue.  As a result, it will force sellers to be a lot more cross-functional in their role by having short feedback loops with folks from product, engineering, marketing, design.


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