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Design Leadership in a Startup

Summary

Developed a clear vision and strategy, built culture and repeatable processes, and supported the growth of individuals – while leading the design of highly complex features and systems.

Skills Used

Influence, Vision, Strategy, Team Building, Process Design, Systems Design, Prototyping, UX Research, Design Thinking, Hiring, Coaching, Mentoring


The Role of a Manager and Leader

Build Happy Teams & Strong Culture

The happiness, productivity, and performance of individuals and teams are influenced by their environment. A design team, individual designers or researchers, and everyone they work with are more successful when operating in an environment of trust and psychological safety.

Provide a Clear Vision

Teams are most effective when they are operating with shared values and a shared sense of purpose. Getting desired outcomes requires defining what those outcomes are and aligning the team on them.

Create Good Process

Designers work closely with (and depend on) other teams and disciplines including engineering, product management, marketing, and customer success. Having (just enough) process is critical to cross-functional collaboration and company growth. Establishing process requires a great deal of influence, often without authority.

Leading Design at EverTrue

EverTrue is an Enterprise B2B platform that aims to help universities raise more money by identifying their best prospects based on a variety of signals from numerous data sources. Delivering on this long-term vision required a strategy to invest in the infrastructure and design of our core funcionality.

As Head of Product Design, over the past year and a half, I aligned cross-functional teams on a vision, identified desired outcomes, and managed through frequent obstacles to achieve those outcomes. The following describes how I approached these challenges.

Knowing Your Users

The first tenant of user-centered design is that you must know your users. I was jumping into a new industry, and the only knowledge that existed about our users lived in people's heads. I needed to get the organization aligned on who our users were.


Aligning on Purpose

There was no strategy connecting the work to the vision. People didn’t understand how their work was making a difference. To address this, I Ied an effort to define our core product principles. The six key ways we deliver on our vision. We refined and iterated on these principles over a couple of months until they felt solid. Each of the principles:

  1. Is actionable, concise, and memorable.
  2. Describes an outcome without defining how we get there.
  3. Helps us prioritize our work by evaluating its impact.

Building Culture & Process

I joined EverTrue four months into the pandemic. I’d been working remotely for six years. While previously remote-friendly, there was a strong in-office culture, and communication was suffering from a lack of remote-work fluency. Written documentation was a major weakness and when it existed it was lost in Google Drive, undiscoverable to anyone who didn’t already know it existed (often even then).

To improve the situation I Introduced a modern knowledge workspace tool, helped define best practices, and drove adoption across multiple departments. I also shifted our approach to be hypothesis-driven and created a framework for cross-functional teams to build living PRDs for their projects. Over the span of a few months, the quality and consistency of project documentation increased significantly with 100% participation.


Building & Nurturing Teams

Having clear outcomes defined, it became clear that we didn’t have the right team structure to deliver these outcomes.

I influenced our VP of product and VP of engineering to combine two undersized scrum teams. I also assembled and led a cross-functional team to coalesce around a strategy for a specific project that was a dependency for one of our long-term outcomes.

I introduced new rituals and led team-building exercises to help these teams evolve through the stages from forming to performing. I taught design thinking and virtual white-boarding sessions to make meetings more inclusive, collaborative, and fun. I continued working closely with these teams as a design lead to deliver outcomes.


Hiring & Employee Experience

Hiring is a time-intensive process for the whole team, especially in a startup. Much of this work falls on the hiring manager, but designers and engineers need to be involved, and preparing and conducting interviews is highly disruptive to their work. Our interview process was ad hoc and team members went into interviews without prior coordination, and no clear rubric to base decisions on. Onboarding was also described as 'trial by fire'.

I partnered with our VP of engineering to design an intentional interview process that could be adapted to design, engineering, and PM roles, along with hiring standards that reduce bias. By having clearly defined interview rounds, standard criteria, and a grading system, we significantly improved the experience for both candidates and hiring teams.

We also designed a 30-day onboarding process which includes a dedicated onboarding buddy, and checklists for the new hire and the hiring manager to ensure everything goes smoothly. When I used these processes to hire our second designer it garnered the first 10/10 onboarding rating in company history.


Support and Growth

Designers want to be supported, feel valued, and know that their voices are being heard. They also want to have a career path, know where they're at on it, and how to advance. As an organization, we didn’t have any career ladders defined.

Support starts with effective 1-on-1s. I've read countless articles on best practices and recommendations, and have learned to adapt them to each individual's needs. My most important jobs are to listen well and ask good questions. Once I understand a designer's current needs, I use tools like coaching, facilitation, influence, and advocacy to support them or improve the situation.

I developed a career ladder based on industry research, which defines levels and titles and the skills and expectations for each level. This framework provides structure for regular career development conversations. My work here also helped inform the soft skills expected at each level for other disciplines, and we aligned on parallel management and IC tracks across design, product management, and engineering. This provides a career path as an IC and ensures that management is treated as a lateral move and not a promotion.


Achieving Outcomes

We were occasionally derailed by sales-driven needs and lost several engineers and two PMs at inopportune times. I assumed the role of product management to get critical projects over the finish line and managed a beta program with a bumpy start to a successful outcome. As a result of focusing on happy empowered teams, we were able to achieve a lot despite small teams and frequent obstacles, including:


Reflections

Relationships

Leadership is all about building relationships, which requires a high level of intentionality in a remote environment. As an introvert, it also takes effort, but it is the only way.

Feedback

Building a culture of feedback is challenging but important. From making sure people feel appreciated and their accomplishments are recognized to turning problems around quickly. An environment that provides feedback is perhaps the fastest way we learn.

People Management

I previously hired and managed a team of designers and researchers, but I was the lead individual contributor in my last two roles. I get a lot of satisfaction out of coaching and helping people grow, and from designing systems that facilitate great work. I still love practicing the craft of design, but it doesn't have to be my primary focus.




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