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    How to take control of rapid growth in a bootstrapped startup with outsourcing

    The Complete IT Outsourcing Playbook

    When your bootstrapped SaaS startup is growing through the roof, you need all hands on deck to handle rapid growth. For this, you might consider the three options– do it yourself, hire more people, or outsourcing.

    Doing things yourself at this stage would mean getting bogged down in operations and execution instead of spending your time on more strategic growth tasks.

    On the other hand, hiring could be a worse option as your project requirements change fast, and in a month or two, you would consider reducing your team size.

    Hiring on markets with a high talent shortage is not a piece of cake as you would probably compete with the giants like Google and Facebook.

    In this article, I will show you how to use outsourcing to achieve a high level of flexibility in managing a bootstrapped business that has entered the phase of rapid growth, yet isn’t quite ready to hire on a bigger scale.


    We will look into the three most important domains of growing a bootstrapped tech startup: development, marketing, and operations.

    1. Outsourcing development in a bootstrapped startup

    Speed is everything, especially for a tech business operating in a competitive environment. When planning to build a new feature, one needs to act fast. 

    Instead of utilizing limited development resources, you can support your team of developers with more freelance or agency developers. Here are the benefits of using external development help:

    • More flexibility as you can decrease the development team after you have issued another product update or new features.
    • When working together with more experienced developers, your team can adopt new development techniques and remote work practices. 
    • You cover the knowledge gap in the domains where your team lacks experience, such as a new framework.
    • You are speeding up the development process, cut time to market, and start generating revenue on a new product update faster.

    Where to find the best developers for a bootstrapped startup?

    There are plenty of freelance portals where you can find freelance developers. You can also run your online research to find tech agencies with teams on board. 

    We have covered the process of finding the best teams in these blog posts – check it out!

    How to Hire Developers in Eastern Europe for a Startup [2020 Cheatsheet]

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    Where to Look for Developers from Eastern Europe

    Here are some of the platforms pros and cons.

    Marketplaces like Upwork and Toptal

    alternatives to upwork

    1. A big choice of freelance developers and agencies
    2. You can start working with developers, available just now
    3. You can read what they clients say about them and browse portfolios
    4. Decide to work in the fixed-price model or pay per hour
    1. Great talent gets lost among low-quality suppliers
    2. Mostly freelancers, not full-stack tech teams
    3. When finding a developer through e.g. Upwork, you can’t move your cooperation out of the platform; thus, you will have to pay Upwork commission every time you start a new project.

    To sum up, you will succeed with Upwork if you have a lot of experience at hiring procedures, can vet developers and know exactly what skill set you require.

    Your research  on  Google

    bootstrapped startup outsourcing tech
    1. You can avoid fees you would typically pay to marketplaces (that sometimes amount to 20%)
    2. You can check more information about developers by reading reviews about them on third-party websites
    3. You can run background checks on potential tech partners online
    4. A great learning experience
    1. Time-consuming as you have first to create a list of potential partners, run checks and interviews
    2. You can still find fake reviews or just “half the truth” about a tech team
    3. You don’t know how many of their projects failed not mentioned in in their portfolio or on Clutch


    1. Get matched with the teams that have only positive project history and whose work received 100% client satisfaction
    2. Free of charge
    3. Get a couple of teams that fit your project requirements within 72h
    4. Time saved on due diligence and tech interviews
    5. Support and advice across the process before signing a contract and during active work (tips on negotiation, planning backlog, remote team communication, and management)
    6. Concierge-type and personal approach to your business case
    1. A smaller talent pool than Upwork or Toptal
    2. No instant matching like on marketplaces – it takes a few days until you are being matched to a contractor

    2. Outsourcing design in a bootstrapped startup

    When looking to redesign your app interface or landing pages, you don’t need to hire a full-time designer or team of designers. 

    Speed and elasticity would probably matter to you the most when scaling up your bootstrapped online business. 

    By cutting time on the redesign, you can launch your new product UI that is more user-friendly and can help boost conversion. 

    By working with an outsourced design team, you can put all hands on deck to launch a new redesign faster and decrease team size when your project requirements change.

    Now, you have decided to work with an outsourced team of web designers and UX experts. 

    Let’s explore what you need to do to find the best freelance web designer or a design studio for your bootstrapped project. 

    1. Check their portfolio

    Portals like Behance and Dribble are an endless source of inspiration and a place where you can preview some of the designers’ work as the first step to your selection process. Taking a look at their portfolio will help you understand the level of designer’s experience and the types of projects they work on most of their time.

    Therefore, if I were looking for a web designer to perform SaaS redesign, I would choose professionals who create design predominantly for SaaS.

    outsourcing design in a bootstrapped startup

    2. Check remote management skills

    Find out if your designers follow a transparent and standardized plan for the design process. Ask how your cooperation will look and expect them to explain to you a step-by-step design process. 


    Experienced web designers should be able to break down a bigger goal into smaller milestones and adequately communicate this process. Here is how our designers communicate it:

    how to outsource design in a bootstrapped startup

    Look for a design team that feels comfortable using digital channels for remote communication and keeps you updated on the progress.

    Some designers would under prioritize the importance of processes, transparency, and seamless communication. I recommend staying away from such designers as the neglect of the essentials of remote work will lead to shifting deadlines, misunderstanding, and rework.

    3. Updates on progress & transparency

    You, as a client, need to be informed about each milestone achieved. Even if things go wrong or for some reason, one has to shift deadlines, your designers can’t just sweep issues under the carpet, but keep you updated so that you have full control over the situation.

    how to outsource design in a bootstrapped startup

    4. Documenting requirements

    Your team of designers should have as much information about your project as possible as it will help them understand your project goals, give you a more precise quote, and cut reworks. That is why they have to send you a brief that you have to fill in. In this brief, you will find questions regarding your customer persona, brand voice, and competitive analysis.

    Here is how our designers lead the process of gathering this information:

    how to outsource design in a bootstrapped startup

    If you want to get a recommendation on design teams or work with the designers we have tested out on multiple projects, get started here.

    3. How to find the best marketers for a bootstrapped startup

    1. Find out about their experience

    When vetting new marketers for the Trustshoring talent pool, we always try to engage them in some of our company projects before recommending to clients. 

    This way, we can ensure marketers we would recommend to you or another company live up to the highest market standards. The first thing we are looking at is, of course, a portfolio. 

    Here is how a marketer or marketing team should pitch their potential engagement:

    hiring outsourced marketers for a bootstrapped startup

    2. Check communication skills

    When having calls with the shortlisted candidates, you will learn about their communication skills, especially English proficiency. You can also find out if they are well-versed in your industry and process new information fast. 

    At this stage, you should already expect them to mention a few ideas on strategy and implementation. Also, after learning a bit more about them you will understand if you have a personal fit and will like working together.

    3. Look for an analytical mind

    Marketing is no longer a creative field only. This industry is increasingly more data-driven than it was a decade ago.

    You should be looking for a marketer that can set benchmarks and goals, know what metrics to use, and report progress.

    If I were you, I would ask a few simple questions to discover how well-versed a marketer is with analytics. Here are the examples of interview questions you can use to test for this skill set:

    • What goals would you set for the project?
    • How would you measure that we have achieved our goals?
    • How can I check what users do before they achieve a goal on a webpage? 
    • Can you have a 360-degree overview of a customer (what pages they have visited and where they came to the website)? Could you walk me through the process in Google Analytics?

    Answering all of these questions is essential. An independent market should have to measure the success of their activities and be productive at basic reporting, at the very least. If you notice a marketer is rambling around Google Analytics, this is a sign they are not using it regularly.

    By the way, here is where you can track conversion attribution on your webpage. Go to your Google Analytics account > Conversions > Goals > Goal Flow:

    how to attribute goals with outsourced marketers

    4. Check if they go the extra mile

    Work with a team that dedicates your attention and is ready to do more than required for your success. That is why you have to check if this team is determined to work with you.

    When working with one of the clients in SaaS Motor, we were asked to do a small assignment. This task required showing some examples of email automation we worked on in the past and explaining the logic behind the scoring campaign and email sequences. 

    Some marketers would give up as they would have nothing to show. Others would take their time and send a recording in a week or so, while others would follow our approach – respond within 30 minutes after receiving an online assignment.

    As a result, we got accepted for the project within the next week.

    hiring outsourced marketers for a bootstrapped startup

    There are many more aspects I consider crucial when choosing marketers – regular remote communication, weekly updates, reporting on progress, accountability, responsiveness, and more.

    4. How to find the best virtual assistants for a bootstrapped startup

    1. Focus on conversion

    Competent virtual assistants don’t generate a cost for just answering tickets. That’s precisely the opposite – skilled virtual assistants can contribute to the increase in your conversion rate, sales, and help cut churn. 

    However, as this industry space is extremely crowded, you might come upon outsourced virtual assistants that focus mostly on counting the time they spend on supporting your business instead of real impact.

    Get a feeling of what matters to virtual assistants the most – just work to be done or boosting your business metrics.

    2.  Check their industry focus

    For example, some outsourced virtual assistants focus on supporting SaaS businesses. SaaS industry is specific and needs beyond general expertise to cater better to its customers. Just take an example of failed payment recovery

    There is a big discussion about this on Internet forums:

    failed payment recovery outsourced virtual assistants

    Unfortunately, automated messages and reminders fail at dealing with this problem. An experienced virtual assistant can deal with this better – having tested hundreds of personalized emails to customers, they can make a real impact on cutting your business losses by resolving this single issue. 

    3. Check what languages they cover

    If a big chunk of your clients comes from the countries where English is not a native language, you should consider offering customer support in their native language. Take a look at the statistics for language support at

    outsourced virtual assistants for a bootstrapped startup

    Also, some nationalities like the Japanese prefer speaking with native speakers and can easily spot the difference in accents. That is why having virtual assistants covering multiple languages for customer support is of significant advantage.


    You have learned a few approaches that will help you find your trusted outsourced team of developers, marketers, designers, and virtual assistants. I hope that armed with this advice you will be able to reduce the risk of choosing wrong contractors. Now is the time to apply knowledge in practice and give outsourcing the first try to get things done!


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    Victor Purolnik

    Victor Purolnik

    Founder of Trustshoring

    Contact me

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