Tactical advice on team building with Riley Long, former talent head of Joymode, DogVacay, and Dollar Shave Club

Jess Li
6 min readJul 21, 2020

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I spoke with Riley Long, founder of Connors Long and former general manager at Safire Partners and head of talent at Joymode, DogVacay, and Dollar Shave Club.

Riley Long

What are the biggest mistakes heads of talent make when thinking about team building?

The biggest mistake companies make when thinking about team building is prioritizing speed, both Time To Hire as a core KPI and the broader motivation that drives that KPI being put into place. The motivation that is driving here is that speed and moving fast is better, which in large part is true for startups. That motivation is not the problem, but there needs to be a slight adjustment in realizing that extra thought will allow the entire team to move faster, hire faster, and achieve their mission faster.

Time To Hire is a great metric to assess overall recruitment, but can lead to improper prioritization of moving quickly. Create full clarity around the role and fit by taking an extra day to poke holes in job descriptions and force deep thinking from hiring managers. The clearer a team is about what they need, the easier it will be to both qualify and entice potential candidates, which are the two key areas that teams should be focusing on. Most importantly, the team will be better prepared to onboard the right candidate and that candidate can/will produce results faster.

What is the biggest talent related challenge facing companies?

Every company struggles to feel like they are attracting the ‘best candidates.’ The biggest challenge is understanding what ‘best candidate’ means to your company, your team, and this role. Once we have clarity there, it becomes more simple to figure out where in the recruitment funnel we need to add some extra effort (i.e widening top of funnel by reaching out to more candidates, increasing conversion of candidates by spending extra time selling them on the opportunity, tightening the qualifiers lower in the funnel by adding in new interview questions and projects.)

Here is a high level framework to help gain clarity on what the ‘best candidate’ looks like for your role and team:

First, let’s assess our risk profile for this particular role. Here are some easy ways to think about this with two ends of a spectrum.

High Risk Profile — We can afford to get this hire wrong and can manage this person out in 6 months. This person can learn as they go and we can get them the training they need.

Low Risk Profile — If we get this wrong then the company might not survive. We have an opportunity to accomplish things right now and don’t have time to let this person learn as they go.

If we have a High Risk Profile, we can widen the top of funnel — meaning getting this job in front of more candidates through posting and reaching out. With more candidates coming through, then focus qualifiers through the interview process on culture and upside.

Qualifiers to assess culture and upside should be based on company values. Create questions that produce real world examples of candidates living these values. Think deeply about your values and what it takes to succeed within your environment, then give a shot to somebody that embodies those characteristics.

If we have a Low Risk Profile, then we need to narrow top of funnel — meaning we need to look at candidates that have solved very similar problems before. To find these candidates, identify what problems are being solved by the role and think through what other companies have solved similar problems, when they solved them, and what people were there solving them at that time.

Finally, a great culture is produced by a mixture of people who have done it before and people who have been given a shot. Both energize each other and learn from one another.

At what point should startups think about building out their own talent teams? When they do so, how should they start (i.e. first with recruiters or first with a head of talent)?

The CEO / Founder should always be the best recruiter for the company. They likely have the vision, care the most about success, and have already convinced VCs to give them money against that. Depending on how much support they want or need to be the best recruiter should help them answer that question. A first time founder, somebody in a new industry or location, or somebody who has to prioritize being client facing should first consider a Head of Talent instead of recruiters.

How does team building vary depending on the industry?

I think team building varies more based on size and scale of company rather than industry. The type of talent we are looking for will vary depending on industry, but the ways in which we need to manipulate and care for the recruitment funnel and process is similar for startups.

How does team building vary in different functional areas (i.e. marketing vs. design)?

Some functional areas have skill sets that can be more objectively tested (performance marketing, engineering). The solution to quick growth in those areas is constant refinement of the process and over time there will be enough folks that like the team and that the team like. In an area with a less objective skill set (design) then we need to support hiring managers to figure out a way to get to a yes/no on skill set quicker. In recruitment, we are trying to make an inherently subjective process more objective.

With design as an example, the portfolio is usually the factor that leads to a yes/no. Our goal is to help train the muscle for the Hiring Manager who needs to get to a yes/no faster when looking at portfolios. Ask questions and sit down and go through portfolios together. Ask why — a lot. Force good answers and deep thought. Get them in the habit of saying yes/no quicker and quicker with clarity.

Leadership roles may also seem highly subjective based on fit, so we need to draw back to an earlier framework and tie a scorecard for executive hiring back to the problems this leader will come in and solve. For example, team size, team growth, P&L ownership, P&L size, fundraising, marketing spend, revenue managed, revenue grown, exit, etc. All of these are objective and can give some structure to the recruitment process for leaders. When we add in the layer of fit (subjective, soft skills) then it becomes difficult to measure. The more seasoned a hiring manager, founder, or leader is then the easier it is for them to see fit for their team and the entire organization. The less experienced, the more guard rails we need to put on this. Values, cultural signals, and multiple experienced interviewers are great anchors to pull questions from. The goal of these questions is to get real world examples of these executives living out the company values and awareness when they have not and how they would have to adjust.

What is one piece of advice you would give yourself in your previous talent roles?

Take a day. Take a breath. Think deeper. Any action that involves a human with their own motivations / incentives / drivers deserves that extra time to make sure they align with the team and company. That extra time will make your job easier and will make the company perform better.

How did you take learnings from each talent role to the next?

Growth mindset is something I talked about before I really knew what it meant. To be able to fail and see the learnings is a beautiful thing. There is room for learning and improvement in everything that we do. Be curious, learn more, and then remember what you have learned. The biggest learning that I continue to have is patience. We want to move fast and time certainly is our biggest limiting factor, but good talent decisions can lead to high performing organizations in ways we can’t even imagine in the moment we’re making those decisions.

How did you decide to found Connors Long and what are you most looking forward to?

I’ve seen so many sides of talent acquisition and have always been the most energized and at my happiest when I’m sitting with (or zooming or calling in today’s world) founders, leaders, and builders of companies. When they give me the biggest pain point in the organization it usually comes down to the people working on those problems, or the people that aren’t there yet to work on them. I’m looking forward to really changing the way that those leaders think about and interact with recruiters. I’ve been there alongside a Seed company figuring out how to clean a popcorn machine. I’ve been there through exits. I’m excited to help more people.

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Jess Li
Jess Li

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