Elena Krasnoperova has hired a number of freelancers and contractors on an on-demand basis for graphic design, marketing, lead generation, web research, and software development. At the Bootstrapper Breakfast on July 7 in Palo Alto she shared lessons learned from a range of experiences–both good and bad–and offered some tips on hiring on-demand talent. She was kind enough to allow us to publish her handout as a blog post.

Elena Krasnoperova is a former executive at eBay, PayPal, Zong and oDesk, the founder of two bootstrapped companies in the “family tech” space: SimplyCircle and Calroo, and a Limited Partner at 500 Startups. She is a lifelong learner of all things business and entrepreneurship. Elena holds a Ph.D. in Psychology from Stanford University

Top 10 Bootstrapper Tips for Hiring On-Demand Talent

By Elena Krasnoperova, founder of Calroo  and SimplyCircle.

1. Delegate as much as you possibly can

I’ve used contractors and consultants, hiring on-demand talent for projects that:

  • I can’t do at all because I lack technical skills (e.g., SW development, graphic design, video production)
  • They can do better than me because I lack certain expertise or tools (e.g., marketing consulting project like app launch)
  • I could definitely do myself but I could get someone else to do cheaply
    (<$10/hour for foreign workers or $20/hour for US-based workers) as it frees me up to do more strategic stuff

2. Use personal referral whenever possible.

Ask your network for referrals. To ask specific people, use whatever method they respond to–email, FB messenger, etc. To ask your network in general, post your question on LinkedIn. I’ve had great results with that method.

Make sure to speak with the referral live to make sure 1) the referral is genuine and recent and 2) your situation is similar to theirs.

Even when you’re hiring someone not based on a personal referral, when hiring a consultant for an expensive project (more than a couple hundred dollars), always make sure to get their references and to follow up with them live. When using platforms for hiring on-demand talent look at their reviews and ratings (actually read them!)

3. Use the best platform for that type of service.

For graphic design, I had good experiences with 99Designs and with Fiverr (see tip #4) – but you use them differently, with different expectations of quality.

For local, high-end ($50+ per hour) marketing consultants, I had success with using LI Pro Finder. (But I also had disastrous experiences with LI Pro Finder consultants).

For software development, I really recommend hiring based on personal referrals (especially if you are not technical yourself). But if you are technical enough to evaluate them and their work, go with either Upwork or Toptal. I highly recommend the firm that I’ve been working with (they are based in Pakistan).

For web research, lead generation, virtual assistants, etc. use Upwork or request an intro from me one of the two companies I’ve been working with. One is based in Pakistan, the other in India.

For customer support, I recommend Upwork. I had good experiences hiring people from the Philippines. (When I was a VP at Upwork, 90% of my own customer support team was from the Philippines, hired and managed through Upwork).

4. Garbage in – garbage out.

You have to put in high quality input to get high quality output. That means writing really thoughtful, detailed Statement of Work (SOW). That means providing timely, actionable feedback throughout the process. That means sticking with it until you get what you need. You, not them, are ultimately responsible for getting your money’s worth.

5. Always start with a small trial project, ideally with several people.

Make sure the scope of work is really tight and simple, so that you can objectively evaluate the quality of the output (accuracy, etc.) and their communication skills.

On Fiverr, ALWAYS hire at least 3 people for every job. It’s literally $5 per project (maybe $15-20 for some extras), so you never want to limit yourself to just one person.

6. Communication skills and receptiveness to feedback matter a LOT.

I switched providers for software / mobile app development because of communication (or lack thereof).

The trial project is a great way of evaluating their communication skills. Make your expectations very clear, spell them out, and get them to agree to them, in writing. For two ongoing projects I have (1 SW / app development, 1 lead generation), I have the respective people send me daily email updates. Every single day.

7. Make sure you’re legally “covered.”

Always have your consultants sign a consulting agreement that spells out confidentiality, the fact that all IP / work product belongs to you, etc. Make sure your MCA includes a detailed SOW that specifies the scope and terms of work.

8. Take great care with fixed price projects vs. hourly projects.

Most clients (myself included) have a strong preference for the former. Most consultants have a strong preference for the latter. Sometimes you can strike a compromise where they will bill you hourly but there are maximums they can exceed for a project.

I got massively burned on a marketing consulting project because of such a misunderstanding. Because she gave me a detailed estimate (spelling out expectations of hours per deliverable), I treated it as a fixed price project when she only delivered a small subset of deliverables, she wanted to bill me for the hours that she said she put in. We ended up compromising somewhat but both sides felt ripped off.

For a while I tried searching for consultants (especially marketing consultants) who are willing to tie their pay to results. They don’t exist. The best I can sometimes do is specify some minimum guarantees (eg get at least 3 placements in major publications, get at least 20 app reviews, etc.). You still pay hourly (or fixed price) but at least you have some assurance and some recourse if they do not deliver the results. (Btw I think there is a business model opportunity for someone if they could make it work!)

Likewise I have never been able to find consultants / contractors willing to work for equity (or even a mix of cash and equity). They all want cash.

9. Hire slow, fire fast.

If something is not working right, tell them – and do it early and often (as soon as you detect a problem and until it gets fixed). Give them a chance to fix it but if they don’t, cut your losses.

10. If somebody is working out great, find a way to help that freelancer.

Great, detailed reviews (if you found them through a platform) and personal referrals to new clients are much appreciated. Some companies have formal referral programs where you might get something for successful referrals. You want to be the best client that the consultant / freelancer ever had! What goes around, comes around.

Hope this was useful! Let’s connect on LinkedIn – send me a connection request and mention this event.

If you want a referral to a great SW/mobile development company, email me at elena@simplycircle.com.