I need a right-hand person to support my growing business and some personal tasks. Someone who can take a bunch of stuff off my plate and figure out the things neither of us has done before. I'm a serial entrepreneur and co-founder of Clarity Consulting, an AI consulting firm based in Inner-SE Portland (Hawthorne neighborhood). Our offices are my 800 square foot home office that doubles as the co-working space for our Portland team and a co-working space in the same neighborhood. It's a real business but it's not a formal one, and you should be comfortable with that. I think this can be a dynamic and interesting role for the right person with a ton of growth potential in terms of responsibilities and compensation. Between the businesses, personal assistant work and assisting with some rental properties I own, there's a long list of things that need doing and not enough of me to do them.
What this job actually is
Initially there is a bit more personal assistant work than executive assistant level work. Cleaning and organizing the house, running errands, showing rentals (infrequent), coordinating maintenance folks, small repairs and whatever random thing comes up that week.
As the consulting business grows I'll need more executive assistant help: scheduling, outreach, calendars, events and special projects. How fast the role moves that direction depends on fit and how you do.
I want to be upfront. There is an opportunity for the personal assistant work to shrink over time and executive assistant for the business responsibilities to grow over time. However… If you want a pure EA job and would be annoyed cleaning a kitchen or hauling something to Goodwill, this isn't it. If you like variety and want to be genuinely useful across a business and a household, keep reading.
- Ongoing cleaning and organizing of my house
- Errands and personal organization
- Helping manage a few single family rentals, including showing rentals and coordinating maintenance workers
- Light home maintenance like small repairs, paint touch-ups, general upkeep and yard work. Not essential but bonus points if you have real handyperson skills.
- Random tasks. Recent examples: troubleshooting a broken remote, selling old items, washing vehicles, returning Amazon orders, recharging batteries.
Executive assistant responsibilities
- Scheduling appointments with existing leads and contacts
- Outbound sales outreach by cold call, email and LinkedIn
- Troubleshoot software issues and assist in solving various business challenges
- Following-up with non-responsive leads to re-engage
- Managing business calendars, event coordination and logistics
- Following-up on overdue invoices
- Researching and trying out new software tools, working on implementing new business processes
- Taking initiative, acting as the ‘project manager’ to get things done
- Helping on special projects
Who this is for
Early-stage career, entrepreneurially-minded people. Someone who thrives in an environment that requires them to be constantly learning and growing. Self-starters. People who are proactive, fine with being handed something unfamiliar and good at working it out. Can be delegated tasks and take the initiative(!) to get it done, even if the path from start to finish is unclear. Use your own brain power to figure out
If you don't know how to do something, ask AI, watch a YouTube video or Google it. Nobody's going to train you line by line, and honestly that's what makes it a good job.
What you need
- Tech savvy, experience working with various software programs like gmail, google sheets / excel, ideally CRM systems such as Salesforce
- Comfortable with hands-on cleaning, organizing and property upkeep
- Organized and good at juggling tasks and changing priorities
- Thrives in creating structure (rather than waiting for someone else to create it for you)
- Quick learner and a jack of many trades
- In the Portland area with reliable transportation. Close to Inner Southeast is ideal since most of the work is here.
- Good communicator
- Personal or executive assistant experience preferred
- Roughly 70 percent in person and 30 percent remote, more in person early on
- Able to pass a background check
Pay and hours
- $21-$26 per hour to start depending on experience
- Opportunity for $30+ per hour or a salary within 1-2 years
- 20 to 30 hours per week, with the possibility of full time after 90 days
- Start as a 1099 contractor with plans for conversation to an employee. Set your own hours, however, the office is open 9-5 Monday-Friday so in-person work needs to happen in that window.
Why it's a good gig
- You'll see how entrepreneurial projects in AI consulting actually work
- Varied work with real room to take initiative
- Room to grow into massively more responsibility over time
- A path into the AI consulting business as it scales. Potential to earn multiple 6-figures within 3-8 years
- Relaxed environment. It's a house, not an office.
- Work with smart people who care about others and the meaningfulness of the work they do
To apply
- Read the entire posting and ensure you are qualified and seem fitting for the role
- Email your resume to
- Schedule a preliminary interview at (see below for essential note)
Answer these questions in the Calendly Booking Link questions under “Please share anything that will help prepare for our meeting” with concise and to-the-point answers
- Are you in the Portland area with reliable transportation to Inner Southeast Portland?
- Why are you interested in this position and what are your unique strengths?
- Tell me about a time you had to figure out how to do something you'd never done before. What did you do?
Pay: $21.00 - $26.00 per hour
Work Location: Hybrid remote in Portland, OR 97214
