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Philadelphia, PA, 19147
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Building businesses in contexts of uncertainty. 

Clearing Away the Small Stuff


Clearing Away the Small Stuff:

A study of web and mobile shops and design agencies


Over the years I have noticed that the owners of web and mobile agencies as well as design shops struggle with one element of their business in particular: though they value their time greatly and have hired help where they can, many still seem to be left with many hours of tasks that are not in their strength. Often the tasks they are left with span skill levels and verticals and are disparate enough that hiring someone to do them is not practical. Examples include everything from finance and HR, to pinging clients for overdue payments and booking flights for team retreats.  

This is a common problem for medium size businesses across sectors that started small and grew but it struck me as particularly acute for these organizations.  The issue is complicated by agencies that are still deciding internally what type of shop they would like to be, i.e. if they, as owners, would like to be doing the billable work themselves, how much they want to hire and where that leaves their roles and the work they need to prioritize. 


What I set out to achieve in this study was the following

  • To gain a better understanding of the different types of agencies, their goals for growth as well as their internal structure. 
  • Learn about what the most challenging elements of their work are and what they are getting caught on day to day. 
  • Explore existing solutions and their efficacy for these users in particular.
  • Explore how we might support agency owners in doing more work that is in their strength.


The primary method for collecting data was in-depth 1:1 interviews lasting between 30 and 90 minutes.  Over the period of 5 weeks I conducted 20 interviews in total: 10 in-depth interviews, 5 additional ad-hoc interviews and 5 follow up interviews. The majority of the interviewees were agency owners and several were freelancers that worked for agencies on a contract basis. 



For our purposes the following are used interchangeably:

studio = agency = shop

founder = partner = owner

Growth or staying small intentionally

In the large umbrella that is 'design work', the agencies I interviewed focus on creating web and mobile apps.  They work for everyone from small companies to Fortune 500 corporations. Almost all of the agencies interviewed were relatively small (4-15 people), do both development and design in-house and have a very high professional standard for their work.

Beyond those commonalities one helpful way of understanding the distinctions can be seen in their goals. It should be noted this framework can be thought of as a multi-dimensional, i.e. non-linear spectrum.

Some agencies grew fast and often put much of their revenue back into the business by hiring developers and designers which the agency owner is responsible for keeping busy and efficient. The partners are smart enough that they can learn almost anything and out of necessity have taken on a lot of operational and logistical tasks. They often work on large (6 month to multi-year) projects for corporations and medium sized (2-6 month) projects to fill in the gaps.

Other partners have decided to keep their business small. Typically they are less than 4 people, though they can have annual revenues close to or exceeding 1 million USD.  They often work with their spouse who manages human resources, billing and/or operations and have a family. Their teams or more likely to be distributed/ work remotely and their work can vary from ground up projects to longer term maintenance work and supplementing larger agencies' work.  When they take on ground up work they are often smaller to medium sized projects.

Several of the agencies interviewed are in the process of determining if they would like to grow their team or continue to focus themselves on billable hourly work. 

Types of Work

Ground up - Soup to nuts from proposal to deliverables

Large scale - Supplement other teams to help with a big project, e.g. a larger 3rd party development and design shop that they have a relationship with.

Maintenance - Ongoing maintenance from previous projects. Often found in shops who have been around for 5-7+years and focus on a certain specific sub-niches and frameworks.


*Sub-specialties or niching within design and development could be used as another dimension to categorize agencies. Examples include mobile and web, IOS and Android, focus on Drupal/Content Management Systems or a focus on hardware…etc. Some agencies focus heavily on one and others are more flexible and fill the talent gaps in their teams with a network of contract help.


Finding 1: Defining the Small Stuff


One critical finding was figuring out what was most challenging for founders, which turned out to be what several of them referred to as ‘the small stuff’.  The small stuff are the projects and tasks that are critical to the functioning and growth of the organization but do not need to be done by the agency founder.

A few examples:

  • Invoicing clients and following up on late payments 
  • Gathering information to help qualify inbound leads
  • Drafting contracts 
  • Scheduling flights and Airbnbs for travel
  • Coordinating with bookkeepers and accountants about tax questions
  • Onboarding  and offboarding team members from SaaS accounts
  • Anything customer service related
  • Scheduling calls and meetings
  • Shipping packages
  • Ordering office supplies
  • Processing receipts and expenses
  • Sending holiday gifts to clients
  • File management

Finding 2: Knowing how to delegate is the problem

Often for smaller agencies or studios who do not have a lot of previous management experience, knowing when and how much to delegate is the problem. For owners who have never worked with an assistant before, (or on a team if they have been freelancers) they perceive themselves as not being able to ask the question, ‘whats on my list that could be on yours.’

For those that are able to ask that question, they don’t perceive themselves as having the time to mess with it, it is just another to do on a seemingly never ending list.  Accordingly they highly value proactive employees, people who can find things to take off the founder’s plate without being assigned specific to dos.

Finding 3: Partners do not give themselves the luxury of focus they work so hard to give their teams


Partners often fall prey to not working in their strength. They do an incredible job trying to keep their teams focused on one project at a time because they know the switching cost of bouncing between tasks. Switching cost was a concept that almost all of the interviewees were familiar with and mentioned unprompted. They also know, that not working in dedicated blocks of time is demoralizing because you are unable to track the progress of your work. 

This often results in the fragmentation of the organizations key resource: the partners. One of the most common trends was the idea that "if I could get only get rid of some of these smaller tasks that I don’t need to be doing I (or my partner) could be much more effective.'  They do their best to block things out but "things pop up all the time and pull me out of my work." I should note that several interviewees reported that they often spend between 30-70% of their day on either internal or external facing communication. “I have meetings with my team all the time and it is killing me” was a common sentiment, as was spending between 2-4 hours a day on Slack alone.

Note: All interviews took place remotely via phone or video call. I was not able to do in-context home and office visits so the above numbers are based on self-reported data.

Finding 4:
As Lives Change, Struggles CHANGE

The biggest pain seems to be at the intersection of high dollar ($200-$500/hour) billable work and something else that the agency owners have come to care about, for instance having kids or playing guitar in a band. Many express that while they were previously able to do 16 hour days when they were in their 20’s, they are really feeling the pain now.

These owners are very hungry for solutions that allow them to do their work and the other part of their life that is now very important to them and are willing to pay quite a bit for solutions such as nanny’s, personal shoppers, people to manage their email for them…etc.

Finding 5:
Client communication is a problem

Client communication in a service such as this is seen as never ending and there is pressure for agency founders to be constantly on call.  This is especially the case if a project manager has not been hired. I should note that only one of the agencies I spoke with had a project manager and the rest had a partner functioning in that role, either explicitly or implicitly. 

Project management is often something that the founder had to learn when they were freelancing as a developer/designer or learned when they were at a different organization.  They often fall into that role and accordingly place themselves at the intersection of their clients and their team. This makes their lives incredibly stressful because very little can function without them. Only one of the agencies I spoke with had set the expectation with their clients that they would not get back to them right away, but that seems to be very rare and even in that case they expressed concern that they needed to constantly be on top of their email.

Finding 6:
A high standard of work Rules out Existing solutions

"We work very hard to put out high quality work to our clients and expect that level of quality on the team as well."

Whatever is done needs to be done to the agencies' standard.  This goes for all of the above ‘small stuff’ such as booking travel, responding to emails, tracking expenses…etc. Many founders express that the difficulty of trusting people with some of these tasks combined with the ad-hoc nature of them leads them to end up doing them themselves.

Existing services and solutions such as hiring someone on Upwork require a lot of time to set up and are seen as hit or miss in terms of quality. Assistant agencies and startups (such as Zirtual, Fanyhands and Fin) are viewed with a default suspicion because if there is a company between them and their assistant, they are unable to ensure their employees are happy and getting what they need. There is also a concern that the quality will not be good enough despite what the agency promises or that it is not worth the risk. Sometimes, though very rarely, organizations will combine several roles into one full time role. Often however this has to be across skill sets and disciplines such as an ‘Administrative Assistant/ Business Development Associate’.

Potential Solutions and Questions that remain

Several questions that remain which may provide an opportunity for future solutions

  • How might we empower partners to work more in their strength and focus on their most critical and billable work?
  • How might we focus in on helping partners with tasks they already know how to delegate?

How might we help agency partners clear away the small stuff?

How might we help agency partners clear away the small stuff and focus more of on their strengths?

This question stood out from the interviews and synthesis as the most pressing and it seems like there are at least several approaches to solving it.

A few examples are:

  1. A one person hourly executive assistant service where a highly qualified individual works with several companies
  2. A hire-and-train-an-assistant service
  3. An assistant match service, with a vetting component such as Toptal to ensure quality.

Based on the above research I believe that #1, the hourly executive assistant service hold the most potential at this stage.  This is an exciting option because it could allow individuals to start their own sole proprietor businesses doing the small stuff for agencies and web shops. A few essential features of this solution (or of any alternatives) seem to be:

  • Highly skilled - Working with one highly skilled person who is very organized and can train themselves to learn tasks, tools and processes they don’t know. The degree to which they are closely able to understand and replicate the founders goals and tone is proportional to their value. For instance if someone would be able to draft emails as well as the founder they would automatically make themselves irreplaceable. 
  • Trust - It is critical that the founders believe they can ‘lean into’ that person and really trust that the work will be done well.
  • Flexibility - Knowing that their assistant is there when they need them but not dependent on the agency when they are not. For instance, a traditional retainer model where an agency books out a smaller number of hours, such as 20-30 per month and the assistant works with several clients.
  • Proactive - They must be proactive in seeking out more work that they could take on and constantly be asking the question of the themselves, 'what is the founder working on that I could take of his or her hands?'
  • Communicative and Clear - They need to be a good employee and team member even when stepping into organizations that are not perfectly functional. This means communicating openly about how they prefer to be communicated with email, phone…etc, what days they are available, what they need to do their work, what they don’t understand, how many hours their clients have left in any given month and what work was completed.  So much of the opportunity for things to go poorly or incredibly well is in this area of management. Accordingly it is critical that they assistant has the ability to ‘manage up’.

Opportunities and Challenges

  • Turn around time - A reasonable turnaround time for a task is in the 12-24 hour range, above that and it become difficult for the founder to delegate tasks because they have to do a lot of thinking as to if it will be done fast enough.  With customer facing communications such as scheduling a call for instance, it would need to be even faster, less than 1 hour in many cases. This is a critical component and is challenging to balance with the hourly flexibility that agencies desire. Traditionally part of what an employer is paying for by giving someone a 9-5 job is the security that they will be there when needed even if they sometimes need to pay them when there are lulls in the work.  There remains a challenge in balancing the need for reasonable turnaround time for many of the 'small stuff' tasks and the number of hours (maybe only 5 per week) that the agency is paying for the assistant to set aside in their schedule. This might not be a problem at a certain threshold of number of hours per month, for instance ~30 hours a month might be a good balance for both assistant and the agency. 
  • Bringing it to market - It is unclear if individual prospective assistants would see this opportunity and know how best to take advantage of it. This could point to some type of training that walks them through how to do from marketing to the day to day. Another options is a Toptal model that could function as a marketplace while allowing trusting relationships to develop. 
  • Scale - Another challenge is that this solution is not scalable. By definition if the individual Executive Assistant starts taking on help, the become an agency themselves which runs into the trust and transparency issues mentioned in Finding 6. That said, it seems as though some of those concerns could be overcome over time if trust had been established with the initial assistant.


Thanks and such

I would like to thank the very kind and hard working owners of the agencies I spoke with. They were generous with their time and open in sharing their struggles.  I would also like to also give credit where it is due to Jan Chipchase both for his Field Research Masterclass and his incredible archive of work that I have learned so much from, including the basic structure of this report.