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"Great things are done by a series of
small things done together."
-Vincent Van Gogh

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Scaling a software business is hard. Evolving from a PowerPoint deck and a dream into a real business involves so much more than just a solid vision. Every company's journey is certainly unique and will bring a distinct set of obstacles to overcome, however, there are a number of common challenges that all organizations - regardless of industry segment, mission and value proposition - will uniformly encounter as they progress. The first major battle that must be conquered is establishing product-market fit.

 

Can we build it? Will they buy it? Is there actually a
market here?

 

Proving this out involves a healthy dose of blood, sweat, tears and intellect; and many organizations simply never make it past this point. For those that do, the next critical question they must answer is:

 

How do we scale this thing?

 

After product-market fit, building a consistent, predictable, high-performing sales engine is arguably the most difficult challenge a business will encounter. At PeakSpan, we spend a huge portion of our time working with the amazing entrepreneurs we partner with on this very topic. Getting your first sale is incredibly difficult but building an engine that produces on a continuous and predictable basis is a whole different level of challenge.

 

Why is that? If you can sell your solution once,
shouldn't it be easy to sell it again and again?

 

There are so many factors at play and complex variables to consider to really understand the root of this impasse, but at the highest level there is a simple analogy that aptly captures the dynamic we so often observe with growth-stage businesses: youth sports. For anyone who played a sport growing up, remember that one kid who was just WAY better than everyone else? Basketball, baseball, soccer; the sport didn't matter.

Every town had that one athlete who just seemed to be leaps and bounds above everyone else. Give her the ball and she'd score 30 points with ease ... throw him a pass and he'd make the defense look silly as he trotted into the endzone.

Companies that are able to show success with sales in the early days almost always have one of these star athletes. Be it the founder - selling the vision that drove her/him to start the business - or an early hire, who was able to absorb the value proposition by osmosis, consistently producing without ever needing a "tool", supporting resource or any meaningful guidance to make it all work.

Like the street performer who is able to pump out studio-quality beats with incredible precision from nothing more than a few tattered paint buckets and a makeshift pair of drumsticks, the early stage sales hero is able to navigate a complex dialogue and land a customer win without a sophisticated set of enablement tools or well-defined playbook. That's an amazing asset to have when you're an early-stage business trying to survive and prove that you can deliver on the sacred vision that inspired you to start the business. But when the company comes to the inevitable realization that cloning that prodigious athlete isn't possible, the organization must evolve to ensure the next 10 ... 20 ... 100 hires you make will be able to produce.

Cultivating a clear strategy, developing a prescriptive playbook and committing to a process-centric approach becomes a necessity. Or else that amazing asset will ultimately erode and transform into a liability that confines the business in perpetual purgatory. Cultivating sustained success in sales can't be based on the premise that every hire is going to be a star athlete. As the company grows and the sales team expands, interactions between the founder/early hire hero and the newest hire are naturally diluted. Knowledge transfer must mature and be proactively and deliberately mechanized. Disciplined adherence to process has to be established as cultural dogma.

Scaling a software business is hard. Transitioning from
founder/hero-led sales to a process-centric machine is
daunting. But nothing is more important on the
journey from scrappy start-up to seasoned scale-up.
There is no silver bullet. You'll make mistakes. But
there are several steps we've seen work over and over
again - things great companies commit to which just
might help guide the voyage:

✓ Optimizing the system, method and process
becomes the foundational pillar of organizational
development:

  • When company vision resides only in the minds
    of a few people, new team members have no way
    of accessing it
  • Distilling complex ideas into simple, easy to
    understand concepts is essential
  • Develop and refine the playbook for success;
    then coach new hires as they learn it
  • Provide tools, promote tactics and prescribe
    techniques to ensure that learning and
    development are continuous prerogatives, not
    one-time check-the-box onboarding initiatives

✓ Demand accountability and measure progress:

  • Process is meaningless without follow-through
    and dedication to adherence
  • Setting clear goals, establishing straightforward
    guidelines and detailing specific activities for
    new reps to perform is paramount
  • Measure and monitor progress toward the goal

✓ Model and plan for degradation of efficiency:

  • Sales will never be as efficient as it was when the
    Founder and the first sellers who spent 20 hours
    a day together living and breathing every element
    of the company's mission
  • You will make bad hires; reps will take longer to
    ramp; many reps simply will not scale
  • Plan for that as you map out scenarios and project
    the resource required to execute so it doesn't come
    as a surprise

✓ Test, Iterate, Repeat - Scale Sensibly with
Data-Driven Conviction:

  • When you've had a sales team of three people for
    years, you're not ready to hire 20 reps overnight,
    regardless of how much cash is in the bank and
    what your latest pre-money value was
  • Lay the infrastructure needed to ensure
    productivity before starting to recruit
  • Hire small cohorts; onboard them with a
    well-defined program; provide them with tools
    and process elements to enable success
  • Then measure, tweak, optimize, repeat

Scaling a sales team effectively and efficiently is one of
the hardest parts of successful company development. It
won't be easy. The road will be rocky, and things will
always go sideways or south at some point. Assume that.
Establish processes and adhere strictly to them.
Demand accountability. Prioritize ruthlessly. Align the
team with clear goals and objectives, and measure
performance against them. Because ultimately,
companies that sustain success - just like professional
sports organizations relative to youth teams - can't
succeed forever based on the efforts of one superstar. It
takes a disciplined, well-trained team to build a dynasty.

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