You’re a startup and the world of possibilities lies at your feet.  You’ve developed a product that can provide value to organizations across the globe.  You simply need to let the world know about you.  Because every dollar counts, you’re OPPORTUNISTIC, and take wins where you can get them - be it non-core customers, unexpected geographies, unplanned features developments for potential clients…  Along with helping support the business, new customers can take you to new places, which can be fun and might even help with PR.  All sounds like prudent startup execution, right? Wrong.

Unless they are part of a strategic plan to propel your business forward, those opportunistic wins can actually hurt your business.  That’s because every move you make, every new meeting you accept and every new customer you chose to take money from, will have an impact on your geographic footprint, customer driven product needs, and of course, your already thinly stretched marketing team.  Let’s explore further.

The Hydra

A Hydra is a multi-headed mythological serpent from Greek and Roman mythology.  Because of its many heads, it was difficult for the body of the hydra to move forward in any one direction, and thus begins the story of too many of today’s startups.

Sea Monster Startup Strategy

All too commonly, a team of really smart people come together and build a cool and compelling product.  They then go out and explore the world to see where it sticks, and keep exploring and keep exploring, never fully setting up camp in any one place.  And because they are working so hard, with longer and longer days, they are showing some growth and feel like they are winning.  In reality, they have become a hydra and have sown the seeds for inefficiency, at best, and ultimate demise, at worst.  Let’s look at some examples:

When I was part of the leadership team for a SaaS company that had recently landed in the  U.S., we knew we wanted to go after small businesses.  So we started running.  

  • Geography: At first, we tried to cover the whole country.  Then we decided we needed to go hyper-local.  Then we tried a hybrid approach.  We struggled with our geographic concentration.  
  • Sub-market #1:  We decided that small businesses with 1-5 employees was our sweet spot.  Later, we pivoted to companies with 20 or more employees.  Later, after we’d added new features, we decided 1-5 employees was a better fit.  
  • Sub-market #2: Lastly, one of our sales leaders was of Latino descent and recognized this sub-market as an underserved opportunity.  Of course, we pursued those customers despite one glaring gap; our product would only be available in English for the foreseeable future.

In each of these examples, the company was pursuing strategies that didn’t align with its competencies, at the time, nor with its vision for the future.

My “Hydra” observations weren’t limited to that one company.  I found them rampant in another as well, this one in the enterprise space:

  • No vertical focus:  We hired and developed regionally focused sales teams and sent them off to the world and said “sell our product!”  As a result, marketing was frequently inundated with requests for vertical-specific thought leadership that supported the initiatives of the various sales team members.  Not surprisingly, marketing struggled to deliver and tensions grew between marketing and sales
  • Geographic footprint creep: We had offices in North America and EMEA which were barely penetrating those markets.  Despite the opportunities in those geographies, the team started to be OPPORTUNISTIC about some customers in Asia, because they could be really big.  This was despite the fact that we could not properly support the customers due to timezone constraints, did not have language capabilities in the product, and still needed to dedicate significant time and attention to our already existing geographies.
  • Focus on competition:  One of the sales teams’ favorite things to say was “F-____ (insert biggest competitor)!”  “C’mon guys,” I’d say.  “Our focus should be on our customers and delivering awesomeness to them.  Do that and the competition will take care of itself.”  The chanting continued.  When Marketing would present a case to go to a conference and I queried why, I was told “because (competitor B) is going to be there and we don’t want to let them own the show.”  A quick review Porter’s Five Forces instructs us to be aware of competitors and their moves, but not to let them set your direction.  Some have said that running your business based off of a competitor’s moves like driving your car while looking in the rearview mirror.

Do these examples sound familiar?  The companies above spent money they didn’t have to burn, wasted valuable time they didn’t have to spare, and accepted customers who wanted resources the companies didn’t have to give.  

The Octopus

The Octopus is a highly intelligent cephalopod that has eight arms that it can use to swim, when not moving forward through jet propulsion.  It’s my view that the best startups act like an Octopus to cohesively move the organization forward, in achievement of its goals.

Intelligent Octopus Startup Strategy

Smart and successful startups align all the resources at their disposal; their product, their domain expertise, investors, etc., and cohesively leverage them to generate a synergistic go-to-market approach.  As a result, the organization gets propelled forward efficiently, effectively, and in a high quality, sustainable manner.  Here are some areas where startups can focus for alignment:

  • Marketing:  Find a toehold in a vertical that can support you and leverage it!  Create white papers and other forms of thought leadership that demonstrate your domain expertise.  Attend industry conferences that are important for this vertical.  Request and leverage customer referrals, that can, ultimately, create a flywheel effect to generate more customers.
  • Product: Make sure your product is optimized to support your target vertical / market.  This optimization could be language, it could be industry specific requirements, cultural norms and expectations,etc.  Your product roadmap should be architected to ensure success and strength in your target market.  Don’t get distracted by fun features that aren’t supportive.
  • Geography: I’m a big fan of the KISS (Keep It Simple, Stupid) method of things.  The more complex they get, the harder it becomes to deliver at a world-class level.  Your sales, customer success / support and product teams should all be present in the same geography you are pursuing.  Complications, such as time zones, when working on the opposite side of the globe, can literally erode an entire work day from your company’s work week.  Trying to effectively work, on a global scale, as a startup, doesn’t put you further ahead.  It simply puts you on a hamster wheel that’s hard to get off from.
  • The Sales Learning Curve: I wish I’d been introduced to the Harvard Business Review article earlier in my career.  It would have saved a lot of heartache and money.  The authors, experienced entrepreneurs, investors and Stanford lecturers, basically instruct us to learn as much about the customer buying process until it becomes a repeatable, turn-key effort (in as much as a sale can be).  Adding additional sales teams and headcount before you’ve achieved this, will increase your “street quota” but also will create compounding inefficiencies and is like adding more gasoline to a fire to try and extinguish it (my words not theirs).

When you have all these elements working together, you get leverage for every dollar that you spend.  You reduce noise, and get clarity of action, because everyone knows which way to row the boat.  Your business is propelled forward and employee morale increases, because everyone enjoys being part of a winning team.  

If you wisely move to new markets where you can further evolve your resources without disrupting your core market success, you’ve now created a self perpetuating set of successful go-to-market practices.  You can “lift and shift” what you’ve learned in one market to the other.  


The problem for the Hydra, is that it spreads itself too thin and runs out of resources before ever gaining sufficient traction in one area.  Fortune Magazine has said that 40% of startups fail because there isn’t a market need for the product and 30% fail because they run out of cash.  You can’t help but wonder, which giant sea monster these companies have the traits of.

Of course success requires an abundance of hard work, and the key is in execution, but if your startup can align its efforts and set a  clear compass direction that everyone can follow you may just be able to avoid treacherous sea monsters and reach new shores.