Awesome People - Ep 101
tips to hire and onboard faster, better ops playbooks
Hi founders and fellow VC Friends!
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In my last newsletter of 2022, I mentioned that I may switch things up in 2023. I’ll share more on that in a few weeks once we get through our backlog of awesome people 🙏. Stay tuned!
Meet Joe Penn, your Fractional Ops Leader 🛠
Joe was introduced to me by Brandon Taleisnik. Brandon is on the founding team and the VP of Ops at On Deck. I’ve always been impressed by On Deck’s speed of execution. They’re ops wizards. Brandon hired Joe at On Deck as Head of Operations and said if he were to give a "cosign," he couldn’t give a stronger one.
Joe was crucial in establishing the company's early no-code infrastructure, external operations, and internal operations. He helped the company scale from a small team to over 300 employees.
Throughout his career, Joe has project-managed everything from major real estate developments to PGA tour events. However, he’s most proud of successfully launching 20 communities in 20 weeks at On Deck.
One little-known fact about Joe is that he previously founded and sold a bagel shop in Detroit, Michigan. Before the acquisition, his bagels could be found at cafes and restaurants across the state and were rated Best Bagel in Michigan. Life goals…
You can hire Joe on a contract basis to support you with internal and external operations. He’s focused on helping businesses from seed to Series B. Joe is a whiz at:
attracting the right talent and quickly getting them up to speed
helping your business communicate more effectively as the business and chaos accelerate
creating repeatable business operations systems to prepare your organization for scale
You can see more on Joe’s website here.
Everything feels difficult in the early days. You will save yourself hundreds of hours of pain by knowing what ops are crucial for scaling, and what can be left disorganized.
Want an intro to Joe? Respond to this email and I’ll connect you!
Joe was gracious enough to share 3 pro tips ✨
Build a repeatable hiring process that moves fast once you’re 5+ people
Your first 20 hires will largely determine the early fate of your organization. We all know the adage: A players hire A players, and B players hire C players (and many of them). So how do you ensure you're hiring A players as your team scales?
Build a process that:
Encourages self-selection
Has a failsafe
Moves quickly, with diligence
Ensure the right talent for your company is self-selecting into your process and poor fits self-select out. This starts with how you portray your employer brand to the world.
Is your startup for polymaths who are enticed by the highlighted education benefits you show on your careers page? Is it for hustlers who see that "extra hours are rewarded"? Is it for world travelers who are comfortable with near-entirely async cultures?
Your employer brand determines if your hiring funnel is filled with top-tier candidates or if it’s a heap of noise and an expensive waste of time. An important note here: don't hedge your words. Despite how uncomfortable it may feel, draw a line between who is and isn’t a fit. The less you reveal about your culture and mission, the more you hurt yourself and your candidates.
Check out these companies for inspiration on clearly articulating employer brand:
Another crucial element to ensure that you're hiring the right early talent is to have a fail-safe during the recruiting process. This person is ideally one of the founders, or at the very least, somebody who deeply understands the company's soul. The fail-safe's job is to be the last interview. They assess if the candidate is culturally additive and if they raise the talent bar.
Here's the key: the fail-safe has an ultimate veto on the candidate. It has to be culturally acceptable to use that veto as often as needed. At times during hypergrowth at On Deck, this veto was used in 20%+ of our final interviews. Vetoes ensured that we brought on the right talent. Admittedly, it's a poor outcome to let a candidate get to the end before getting vetoed. But, it's a catastrophic outcome if they get hired.
Have the fail-safe interviewer share detailed reasoning behind vetoes to improve your hiring process.
Finally, a word on process and speed: a concrete process allows for speed. Speed breeds excitement. Excitement wins candidates. The number of candidates we closed from application to offer in under two weeks vastly outweighed the number that took longer than two weeks to close. Top talent is often being pulled in many directions and you have to move fast.
Get your candidate to think about your company every day for two weeks. One of two things will happen:
They’ll self-select out because they've spent enough time thinking to know they aren't interested (good outcome)
They'll sell themselves and join your team full of energy to start building (more likely)
Ensure you have a concrete interview process (from the first interview to final approval) before opening the position. Process allows you to move quickly without sacrificing diligence.
A different team member should chat with your candidate every two days. Interviewers should come from different parts of your organization to give the candidate a sense of onboarding before they’ve even accepted the job. In between interviews (assuming all is going well), hiring managers should text or email the candidate to ask about the conversations and share any exciting company updates.
Of course, there is a line here — you don't want to appear pushy or overbearing. But top talent wants to be immersed and excited about their next move. The best way to achieve this is to maintain a quick yet comprehensive and diligent process.
And if you feel the candidate isn't right for the job in the end, there's always the veto!
Everyone in your org should no-code to move faster
Engineers are expensive, everybody needs something from them, and their best work requires uninterrupted blocks of deep work time. When you have an opportunity to take an aspect of the business out of an engineer’s inbox, you should take it. This is why everybody should no-code.
No-code allows anybody to build MVPs, tools to increase their daily efficiency or troubleshoot issues with the platform. This saves your engineering team time, discourages learned helplessness amongst your team, and brings the team closer to the product.
In On Deck’s first few years, we built almost everything — our CRM, onboarding flow, analytics dashboards, email campaigns, internal workflow tools, community management protocols, the list goes on… We used:
Airtable
Zapier
Typeform
Webflow
No-code allows your organization to move at an unparalleled speed during its earliest stages. It’s worth a week or two for everyone to learn the tools.
A word of caution, keep an eye on the use of these tools as you scale. No-code is still nascent, and it can become brittle with time and pressure. As a general rule, if a no-code automation or system is mission-critical for >6 months, it's worth dedicating engineering resources to build a version that can scale with you.
Playbook everything to move faster
As you scale, you'll encounter the monumental challenge of transferring years and months of institutional knowledge to new employees.
This moment is critical – you need to clear your plate so you can take on crucial new projects. Still, you're afraid that in the handoff process, your new employee won't understand all the duct tape and that the system will break down.
This is why playbooking is a cornerstone step toward scaling your organization. Playbooking is the defined and repeatable process of getting things out of your head and down on paper. Playbooks allow someone else to execute tasks with minimal follow-up questions. The alternative is your bandwidth is permanently full, and you can't move on from early projects you led in the organization.
So why haven't you playbooked everything yet? Because it takes forever. And your plate is full, right? Here's a suggestion: take a Loom every time you work on a project you'd like to hand off soon. Explain a bit as you go, but no need to take too much extra time. Good starter tasks include:
Client delivery procedures
Sales cycle and CRM tips and tricks
Onboarding checklists
Repeatable design norms
After making two or three Looms, send the videos and a short bit of context to a new hire and ask them to create a playbook for the process. This is a win:win – it saves you time, encourages new hires to learn various parts of the business, and contributes to the overall knowledge base of the organization. You'll likely get pinged with a few questions along the way, but it's a necessary and worthwhile tradeoff to get this off your plate. Finally, review the playbook after it's drafted to ensure correctness.
At On Deck, we used playbooks to create the backend automation architecture for all of our fellowships. This process tracked and communicated with customers from customer interest to payment. This was a 10+ hour project for each new fellowship, and we were launching new ones every week! Loom delegation allowed even the newest hires to run the process and saved managers dozens of hours over a month.
Want an intro to Joe? Respond to this email and I’ll connect you!
As always, please let me know if you have any questions and if you want an intro to Joe!
Stay awesome,
Founder of Awesome People Ventures & Talent
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Thanks for the feature Julia! Looking forward to supporting more founders and exec teams in the Awesome People community.