• James

SaaS 101: Set Yourself up for Success When Working with Startup Founders

How to handle the business side of your gig + stay on top of what matters


As a product manager or strategist, it can be difficult to work with founders and co-founders of fast-moving SaaS startups, but by following a few easy tips, you can improve your performance and elevate your success when working with entrepreneurs.

As a strategist myself, visionary entrepreneurs are my absolute favorites to work with. In my experience, these entrepreneurs fall into one of two categories:


The Rule Breakers: These entrepreneurs don't live by rules. They enjoy breaking tradition and quite frankly, don't care so much about the details of how something gets done, why there are challenges with retention, or who the product is built for (or vice versa). The “Rule Breakers” need a great team behind them to make it all happen, and for SaaS products, usually the product person or high traction owner such as marketing owns a large stake ensuring everything comes to fruition. Too much detail in the “how” things get done may not be the best use of time. Try to keep things high-level and positive.


The Detail Masters: These business mavens are mired in the details, and sometimes, it’s difficult for them to get past the minutia in order to see the forest through the trees. Working with these founders can be equally as rewarding when structure and a clear understanding regarding “what’s next” when it comes to measuring your outcomes is known. Marketing without measurement and throwing ideas to the wall to see if they stick may pose challenges with this type of entrepreneur. On the flip side some detail masters may want the total opposite of how they approach work to counterbalance their focus. Typically, that opposite personality makes for a great co-founder who continually moves things forward.


As a product manager (or anyone in a small SaaS startup) working in an early-stage startup, it can be difficult to collaborate with a founder or executive who is incredibly busy—as you may not get the chance to connect with that person on a regular basis. However, communication with your key stakeholders is necessary for success. The million dollar question is: How do you solve this time-management issue and help your vision become a reality—with consistency and transparency—when things seem to be moving at the speed of light?


It’s definitely a tough question to address, but my biggest piece of advice is to devise a process which communicates the expectations clearly and efficiently, in order to meet the desired outcome which both parties can agree too. Yes, this sounds a bit like a contract negotiation and in some ways it is. Ultimately, it’s a contract of trust that ensures both of you, regardless of how detailed or not, deliver meaningful results on a frequent basis. This process is really a testament to how you manage your role within the organization. It’s also your source of truth when it comes to accountability and it can help everyone stay on track with what’s happening on a daily, monthly or even quarterly basis.


3 Must-Know Tips for Working with SaaS Founders


1. Create A Weekly Status Report: One thing I’ve continually done throughout my career is keep a weekly diary, of sorts, that highlights the work I accomplished, the work that was coming up and the status of all my projects. I would typically send this status report between the three most important aspects of any operation: people, product and process. This weekly report, depending on the size of your organization or who you’re reporting to, not only keeps you in check and helps jog your memory, it also lets the viewer understand what is happening at a high level. This is something I would send via email, or oftentimes, I would create a Trello board, which can be accessed at any time. Pro tip: Always try to keep your formatting consistent, which makes things easier to find later on.


2. Use The SWOT Analysis Technique: Another great business report is the SWOT analysis—as it provides a multi-directional approach that helps you understand the company’s strengths and weaknesses, while also identifying opportunities and threats. The analysis provides the founder and all stakeholders a comprehensive understanding on things to be aware of for the road ahead, based on what has been happening within the company. For larger organizations, I would recommend this technique be done quarterly, and for smaller companies, once a month should suffice (depending on the speed at which the company is moving).


3. Keep your KPIs SMART: An objective or goal without measurement is dead in the water. It’s a task that ultimately has zero accountability because there isn’t a clear idea on what is expected from the outcome. Key concepts such as KPIs, SMART goals and OGSMs are wonderful tools to utilize when trying to frame goals and milestones; however, they are also some of the most underutilized tools due to poor application or understanding. One thing that will really set any project manager apart is delivering the KPIs based on SMART criteria. By following the basic SMART criteria fundamentals to boost your measurement and goals, it will help eliminate any unpleasant surprises at the end of the quarter.


I hope these suggestions give you some thought and allow you to take a more proactive approach in developing your own process to apply at your new job, or well into your existing venture. From personal experience—both managing others and having to report to executives, founders and investors—these are all tips I have personally utilized and have had great success with.

18 views