Help me self-educate on scaling a small software sales team?

August 28, 2016 12:44 PM

I have found myself in the fortunate position of having a somewhat senior role in a small, fast-growing software company. Because of my total lack of software/sales experience, I have this strong gut feeling that my approach is "winging it" and I would like to start understanding more seriously what I need to do.

I am in a strange position. My background is in the entertainment industry, and because of this background I was hired by my current company (which sells principally to that industry) and through a series of promotions and employee turnover now hold a relatively senior position. Though it is officially "Customer Success," the role runs the gamut from key/enterprise account management, inside sales, lifecycle marketing, to 'traditional' customer success.

The software is SaaS, and through a mix of a fantastic product and quality referrals from the right customers, we have been able to maintain a positive growth trend.

However, as the company grows I will need to define my role more precisely, and without experience I am worried about missing out on opportunities and being relegated to a more junior role over time. I would really prefer to be a key driver of the company's growth towards profit and ultimately sale, and I think my current approach is probably only halfway beneficial.

What it comes down to is that I do not really understand "the path" that we should be on, and I want to read case studies/biographies/histories of similar sales/account management/customer success teams to understand how they have succeeded. I am sure that we are doing some things right and some things wrong, and I want to better understand through the lens of history what those are.

I am not interested in a lot of the customer success-focused content that gets churned out by companies with an agenda (Natero, Gainsight, Totango, etc.). I am also acutely aware of how many other companies with our business model are revenue-positive but not profitable, and I want to steer clear of emulating those companies. I also have read a lot of essays of the "Growth Hacking" variety and found very little actionable insight from that genre.

If you can point me to anything - brilliant Quora responses, business journals, books that are maybe not SaaS-specific but which offer a proven top-level sales vision, I am totally open to it. Show me what you got, mefites.

posted by sidi hamet to Work & Money (5 answers total)

In my experience the path that you're on will vary wildly based on your overall go to market strategy , and if you're in growth mode you'll be constantly tinkering with what you're doing. I think you're going to need to break this in to pieces - which I hope doesn't come off as a series of rhetorical questions.
1) Do you have the systems in place to understand and measure your funnel. Do you understand how you go from contact/lead to opportunity and are the marketing and sales organizations aligned to make changes and understand them? Are you using salesforce or the equivalent? Do you have opportunities and stage well articulated and is it sensible?

2) Do you understand your go to market sales model such that you can tweak it or change it? Are you direct sales focussed, field sales, geo segmented, target market segmented (smb/corp/enterprise/strategic)? Is any of that important?

3) Does your sales staff understand what they are accountable for and how they are metric'd and measured? Is it activities (calls/meetings/demos/etc)

4) If you have a technical sale, are your sales reliant on having a technical interaction, do you have sufficient technical presales staff to support the sales team? Are those staff well managed and do they know when they should get engaged?

5) Are you building a culture that likes to win, is respectful of the customer, is focussed on the customer and setting them up for success?

6) Are the incentives aligned with the above, uncomplicated, and straightforward?

What I have observed (and my experience is somewhat limited here, but I have been at the leadership coal face for software sales in technical presales) is that you need to first and foremost make sure that the sales team knows what they are accountable for, knows how to execute, and is unconfused about expectations and how to be successful. If you get those pieces right you can work on the other pieces. By far, again at smaller scales, the importance on simplicity and keeping things uncomplicated cannot be overstressed. At smaller scales you do not have the support infrastructure to deal with complicated structures.

Finally, have discussions with the rest of the leadership - is the goal cash neutral so you can continue to invest, or is it to actually return profit to the investors? What is your planning cycle? How integrated is marketing with sales with customer success with finance? Do you have metrics in your business, can you map CAC, ACV, renewal rates, LTV? Do you know what levers impact these?
posted by iamabot at 1:13 PM on August 28, 2016 [1 favorite]

Oh last thing - you should find a mentor for yourself and a 3rd party - an unrelated software sales management consultant who understands your industry and market. Do not make these two individuals the same person. Winging it may work, but in my experience a ton of this is pretty unintuitive and way more programmatic that you think or than winging it allows for.
posted by iamabot at 1:15 PM on August 28, 2016

http://www.forbes.com/sites/robertcringely/2014/11/19/death-of-the-ibm-salesman/#30daa42d8dad

I think at the core, it's not just selling software, but quantifying how to measure different aspects of this, and deciding where to put efforts. Not just in the initial sale, but in also keeping customers you have.
posted by nickggully at 1:18 PM on August 28, 2016

The core of your question:

I want to read case studies/biographies/histories of similar sales/account management/customer success teams to understand how they have succeeded.

is IMO somewhat hard to come by because

- popular business articles and for that matter a lot of case studies focus on much larger companies.

- the lessons of Apple or eBay or SalesForce don't necessarily translate into what you should do as a smaller company,

- survivorship bias skews a lot of the stories (having an entitled prick who isn't much of a software engineer at the helm isn't really a consistent recipe for success, for example)...

- (perhaps a rehash of the last point) - everybody lies. The glorious founding days emerge from the fog of war, and forge a brilliant narrative of how brilliant everybody was.

I'm in a really similar role at the company I'm at. I'll PM you if you're interested in talking further, and assuming we're not competitors we can swap some ideas or at least some hard luck stories.
posted by randomkeystrike at 1:54 PM on August 28, 2016

For more reading, I can recommend The Harvard Business Review. The quality is generally high (much higher than most content farms) and there is a wealth of information, case studies and strategy to help give you a better foundation.

You may also want to look up some self-taught MBA reading lists. While I don't have an MBA, I've benefited from some advisors and mentors who taught in MBA programs, as well as the recommendations above.
posted by A hidden well at 3:34 PM on August 28, 2016