The Early Stage CEO’s Secret Weapon: How to Hire an Operations Assistant

The Early Stage CEO’s Secret Weapon: How to Hire an Operations Assistant

Recently I discovered an entrepreneurial secret weapon, in the form of a new role we created at AVRA, the “Operational Assistant.”

First, I’ll set the scene.

In a little more than a year, AVRA has grown from just me to over 15 people who work anywhere from part-time to full-time as contractors. We work with anywhere from 5 to 10 clients (mostly startups and growth companies) and each client gets a dedicated team—each of which excels at one or more of the 5 Disciplines of Hiring.

As a solo Founder, my roles include: Sales, Operations, Product and People (hiring, management, performance, etc). And as an early-stage company, we are building everything as we go. If you’ve been in a similar situation, you know the feeling: it’s exhausting.

Luckily, I have a right-hand-man, who joined as the second person early on. He has helped take a lot off my plate. My amazing mother, Susan, was our first Interviewer and continues to rock that role and help others on that team. But I’ve still found myself wishing I had a head of operations—there are so many things I know need to be done, but don’t have the bandwidth for.

So what are the options?

Well. I could hire a Head of Ops, but though we’re profitable and growing, we are also self-funded, thus need to keep costs in line with client work. So no fancy COO for me.

Second, I could just have things not get done. Viable option. But subpar.

Third, is what we’ve come to call the Operations Assistant, or the OA (after the Netflix show of the same name… which if you haven’t watched already, do).

The role of an OA

First off, there is not just one OA, it’s not like a COO or head of operations role. You don’t hire one person, then they build out a team. The goal is to have several, so when one is busy, the other’s have the bandwidth. This works particularly well with our model of remote, contract work, though may not work as well if you hire in-house or full time.

The role of an OA is inherently tied to the 80/20 principle, which if you are not already familiar with I’d suggest learning about here (if you want to go deep, read the book). The gist is 20% of effort results in 80% of results. As a founder we need to be relentless in (a) understanding what that 20% is and (b) making sure we spend an outsized amount of time on it.

Easier said than done; and, there is a lot of stuff that has to be done in the 80%, like payroll, research for a project, creating decks, etc. Now you can 80/20 your 80% and get real ninja, but that is another post for another day.

At Avra our amazing Operations Assistants help me with the heavy lifting that needs to be done, but isn’t:

  • Something I love (like writing)
  • Something only I can do (like closing large clients)
  • Something I *have* to do (like signing contracts)

This would include:

  • Research
  • Gathering, analyzing and/or making sense of data
  • Supporting my Executive Assistant, Sarah, when there is overflow
  • Creating, and optimizing, meeting agendas
  • Some project management
  • Process management

Here are three examples of things that have provided a lot of value, that I simply wouldn’t have done if it was just on me.

(1) Podcast appearances = AVRA $$$ or Opportunities

Researching and building a list of Podcasts to potentially appear on, with all the relevant data, the person who books the guest’s name and contact information, and information on the target audience (ensuring it overlaps with AVRA’s client persona). Then handing off to my EA who will reach out and try to get me booked.

(2) Re-doing the way we manage meetings

Running efficient meetings is critical as a business grows past 10 people. There is a science to effective meetings and much has been written on it. But who has the time to read that information, and make a calculated decision based on the company’s goals and culture of what type of meeting infrastructure is best? Not yours truly—not only do I have the attention span of a banana slug, but I simply don’t have the 10 hours. But one of our amazing OAs, do. And they’ll be better at it than I will. Then we’ll test out the new agenda in one meeting, see how it goes, tweak, and roll out to the entire company.

(3) Managing Asana

Work management platforms are only as powerful as the person responsible for making sure they’re used. An Operations Assistant assigned to Asana follows up on projects and makes sure due dates are adhered to, bubbling up issues to the CEO (me) if a problem becomes a pattern.

How to hire an Operations Assistant

Yay! You’re so excited…you imagine so many of the operational tasks on your to-do list falling into the waiting and competent arms of your own OA! But wait…the dreaded hiring process 0_0

No fears, my overwhelmed friend, hiring is our jam…

The thing with the OA role, especially if it’s remote and pays decently, you will have a TON of applicants. It’s very easy to bring someone on who thinks they’ll excel, but in reality, will fail. That’s wasted time…and for operational heavy roles like this, it can actually add to your anxiety if you don’t have someone who is super skilled and highly reliable.

Luckily, you can set up a hiring process the same as we did at AVRA and find several amazing candidates within a few weeks time.

The process we used is below, feel free to adjust + if you have specific questions on it you can email me directly or tweet at me @marenkate.

Filling the OA Funnel

Depending on the type of job, pay, demand for that role, location, and other factors you’ll want to post to one or more of the below:

  • ZipRecruiter
  • AngelList
  • Craigslist
  • Indeed
  • College Job Boards
  • Glassdoor

Then be sure to share live postings through your social networks, both personal and professional.

The Interview Process

Step 1: Application

Collected and managed through Breezy

  • Name
  • Email
  • Resume
  • Location
  • Questionnaire
    • What honestly draws you to this role—please no cover letter jargon—how does this role tie into your professional narrative and/or your future goals?
    • Please take this “Attention to Detail” test + then in the answer box tell us your score. *NOTE: Please read instructions thoroughly! It should only take 3 minutes.
    • If you got this job, when is the soonest you could start and when would your ideal start date be?
    • What draws you to remote work, versus an in-person, stable paycheck kind of gig?
    • Please list your familiarity with the following on a scale of 0 to 10: Google Calendar, Excel, Asana, Google Suite, Trello, Slack


Next Step: Y/N N = Rejection email Y = Test Task (email template in Breezy of same name)
RP: this stands for responsible party, and is the name of the person responsible for this step.

Step 2: Test Task

Subject: Next stage of your application for the Operations Assistant role.


Thanks for applying for the Operational Assistant role at [COMPANY]. The next step before we set up a call is for you to complete a relatively quick travel task so we get a feel for your work style, detail orientation and travel-planning style. Also, you’ll also be able to get a sense of what type of work this job may contain.

Please complete the below travel task and send it back within 3 business days to [CLIENT] to remain in consideration for this position.

If there is something that will delay the task completion, please let us know as soon as possible.



  1. This should take between 30-60 minutes. We want to be effective and efficient.
  2. You’ll be submitting your response in a Google Doc.
    • The title of the Doc should be: [POSITION NAME] Travel Test Task [YOUR NAME, DATE].
    • Format the doc like you would if you were responding via email.
    • Make sure the Doc is viewable to anyone who has a link.
  3. Send back to us with the link to your doc when you are ready for us to review it.

Travel Task:

I have a ton of TrueBlue travel awards points through JetBlue. I’d like to get to Maui sometime this year. Please let me know my best options for flying round trip business class. What kind of partners do they have? Can I use my points to book hotel, rental car, things to do while on the island? Thanks!


Notes: Check how the candidate formats the response email, they should be organized and it should reflect the way they will communicate in written form with clients.
Next Step: Y/N N = Rejection email Y = Phone Screen 1 (email template in Breezy of same name w/ calendly link)

Step 3: Initial Phone Screen

*Remember to pepper your interview with “what, how, why” and “tell me more” to make sure we are really understanding what the candidate is saying.


  1. In only a few minutes, walk me through your career history, or any other experiences, that you believe make you a great fit for this role:


  • To make sure that we’re in line with what you need, what are your salary expectations for this role?
  • What’s the last operational hack you implemented? How successful was it and how did you measure its success?


  • What drew you to apply for this OA role and how well would you say you understand what we’re doing here? This serves several purposes, foremost of which is to make sure the candidate actually KNOWS what the company does. A surprising amount of people will blanket apply to jobs without doing the research. And finally this is a great window into (a) their communication style and (b) their ability to understand and follow instructions.


  • Where did you originally see this job posting when you applied (only if they are inbound candidates and applied through the portal/website)? What was the source? ZipRecruiter, Indeed, Google, Linkedin, college boards, etc.
  • How have you kept clients, or others, organized in the past? How would you deal with a fast moving, disparate team?
  • What personality or character traits bug you in other people? EQ judge, also allows you to see if they are a kiss-ass or not.
  • Who was the most difficult client, or person, you ever worked with? Why, and how did you manage that situation? All EAs sign NDAs, strict ones, if they drop the names of their clients—huge red flag.
    • Follow up—if applicable—what did you do wrong in handling that situation and what did you learn?
  • What are you really good at professionally? Try to get the candidate to list 5 to 7 strengths, asking for examples to help understand strengths in context. This is the first step in getting a holistic view of strengths and weaknesses. Screen out candidates if we see gaps between what the role/company needs and what the interviewee can offer.
  • What are you weakest at, or not interested in doing professionally? If you get cookie cutter responses or “I work too hard” push them for more honest answers: “that seems like a strength to me, what are you actually not good or not interested in”. Talented people will be able to self-assess accurately, sometimes if someone is having a hard time ask them to guess what past colleagues or bosses would say.
  • Who were your last three bosses and how would they each rate your performance on a scale of 0 to 10 when we talk to them during the reference check part of this process? Saying “when” pushes for honesty. After each response ask “why do you think they would rate you X?”, this should allow strong candidates to reinforce and expand on their strength and weakness list. We will want 8, 9s, and 10s. Similar to NPS rating, 7s are neutral—6 and below could be a flag for screening out based on the circumstances. Honesty and understanding of what went wrong and why, is critical in a good candidate.
  • Do you have any questions for us? Regardless of the outcome, we want to show the interviewees respect through this last step… Take notes, good questions can tell a lot about a candidate.


Next Step: Y/N N = Rejection email Y = Paid Test Project

Step 4: Paid Test Project

Test Task:

Hi [[candidate_first_name]],

The next step in the application process for the Operations Associate at AVRA is to complete a paid test project—this gives you a sense of some of the work you may be doing, and also allows us to see how you handle a small project, and most importantly, this is REAL project that will create real value 🙂


High-level Goal: Get @MKD to speak at  least once a month at conferences, whose guests or fellow-speakers fit one of these demographics: Founders/C-level execs/Head of Ops—of U.S. based startups, or startups expanding into U.S; Investors (VC or Angel)


Step 1: Check out the Startup/Investor Conferences 2019 spreadsheet. You’ll be spending no more than 3-hours trying to find as many relevant, conferences that fit the above specifications, and plugging in the variables into the spreadsheet.

Please check the MAIN tab, to see what conferences we already have listed—so there is no overlap—then create your own tab + copy the first row, then you can get started. If you have any questions, do let us know. The pay for this test project will be $XX and you can invoice [REDACTED] for it once complete.

If you want to move forward, please get this back to us within no more than 4-business days.

Resources: Speaking events Maren did in the last 2 years with links:

  • 2xinTech Female Founders Conference: “Do What I Say, Not What I Did”
  • Launch: Scale Maren Kate Donovan: Zirtual lessons $11m to $0
  • Launch Conference, Sydney 2018: Hire, Fire, Reward, Repeat (01:23 is when Maren starts)




Next Step: Y/N N = Rejection email Y = Reference check

Step 5: Reference checks, also known as NEVER SKIP THE REFERENCES.

In a previous post we covered how to best to reference checking, please check it out here. I can’t stress enough how important this step is—and how often people skip it.

Step 6: Decision

Skill: Are we 90% or more confident that the candidate can get the job done because of his/her skills match the desired outcomes from our scorecard.

Alignment: Are we 90% or more confident that the candidate will be a good fit, because what they want matches the mission and competencies of the role, as well as the culture of the company.

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