CHASE: Lessons Learned from a Yearlong Sales Experience

I just completed a 13-month tenure working in sales at Deliverr (acquired by Shopify) and every ending of a journey provides the perfect time to slow down and reflect on the experience. This particular job provided so many unique learning opportunities — being fully remote and part of a rapidly scaling organization that had two 9-figure fundraises along with a multi-billion dollar acquisition in the span of 13 months.

To remember an experience for the long run, I like to come up with a term that symbolizes a particular chapter in my personal journey; for this one, I will always remember my time at Deliverr as my CHASE.

Prior to joining Deliverr, I had spent the past 3+ years working in very early stage entrepreneurial/start-up environments where we were scrapping for every little penny to stay alive. My endeavors ended up all failing so I had many different aspects to my life to CHASE coming into Deliverr — including self-confidence, a clearly defined career focus, respect, contribution to society, strong 2-way relationships, and understanding my place in the world.

Working in a hyper-growth sales organization with peers to share the journey with (and no decision making power whatsoever) provided me with the perfect opportunities to learn some valuable lessons from various life aspects that I will proudly take with me in my future endeavors — C.H.A.S.E.

Connection

A whole-hearted connection to the work and to the people around that work is a pre-requisite to finding success in generating sales and building strong relationships with teammates and colleagues. Without that connection, it’s incredibly challenging to find any sort of success or fulfillment in the work.

A deep internal connection to the work (how to connect with customers, how to package the right solutions for the customers, etc.) brings out inherent curiosity and the willingness to ask questions to several different colleagues that especially in a remote environment allows you to connect with your teammates and present stronger viable solutions to your prospective customers, which in turn leads to success in the work.

Hobby

Sales particularly is obsessively driven by metrics and quota attainment that are always hanging above our heads. The internal pressures from forecasting and hitting quota targets never stops and constantly thinking about outcomes can quickly lead to burnout, depression, and an overall negative sentiment towards life.

Thus, it is IMPERATIVE to consistently disconnect from the everyday workflow to maintain a healthy mind, body, and soul that leads to optimal everyday performance. Most larger scale projects — such as B2B sales deal cycles — can take months to effectively complete with no guarantee of the desired outcome ; all it takes is one unfocused mistake to destroy hard earned good will in both work and relationships. Hobbies — especially artistic endeavors — help keep sanity over a sustained duration of time.

Assets

Pierre Bourdieu’s Forms of Capital re-thought the way I looked at accumulating assets; originally, I thought assets defined money and expensive possessions but as Bourdieu describes, wealth becomes a combination of cultural, social, and economic capital. Building on this, I have defined assets as the combination of these three forms of capital:

• Cultural = Continuously building skills and knowledge in the never-ending pursuit of mastery of your respective craft. The more skills and knowledge we can acquire within a particular focus, the more we can effectively contribute over time and the more opportunities we have to take part in the work we all yearn to do.
• Social = Building meaningful, genuine, trusting 2–way relationships with the right people. In sales, every action is tracked (from outbound communication to meetings booked to deal cycle progression to revenues generated). However, what truly matters in the long run is what cannot be tangibly measured: the kinds of people we surround ourselves with and the depth of trust we have with those around us. Through our struggles, can we lean on our support system to navigate us through turbulence? The people and the level of connection we have with them is a true form of wealth and asset building.
• Economic = the tangible assets we accumulate (money, tangible property, etc.) is the combination of the cultural and social capital we build — the more skills, knowledge, and meaningful relationships we have, the more opportunities arise for accumulating economic wealth.

Structure

Positioning our days with everyday routines with built-in systems and processes helps us maintain focus and perspective on every day. Everybody has their own goals in life — in sales, high level goals are clearly defined by our quota structure. Achieving a clearly specified goal — such as revenue attainment — requires a combination of everyday disciplines, which I incorporate in sales through the 3 P’s:

• Pitch: spending time every day understanding the value proposition and service the company strives to serve a particular market
• Prospect: identifying new potential leads and opportunities to go after through outbound communication
• Pipeline: understanding current deals in play and determining which opportunities need actionable touch points

These three elements of the sales work served as the foundation to my everyday workflow, so I strive to incorporate focused time every day to accomplish this work — the same principles hold true to finding time and structure to take part in key everyday actions — such as exercising, family time, hobbies, etc.

Environment

Building upon the above points, creating the right energy and environment to accomplish your desired goals is EVERYTHING. Working remote, this is imperative as communication between two parties does not happen in the same physical setting. The way managers/leaders interact with the rest of the team members has a profound impact on an individual’s ability to perform well and be well.

A quality manager/leader who cares about our well-being as much (if not more) than our performance and who provides the freedom for us to work to our abilities can truly boost the overall ability to be our best selves; on the contrary, a controlling manager/coach who only cares about numbers and acts as a watchdog can negatively impact the overall wellness of our life at ALL levels, spiraling our lives out of control and losing our desire to work.

The environment and surroundings we build in our lives can either make or break us — it’s imperative to choose our managers/leaders and overall settings wisely.

Connection. Hobbies. Assets. Structure. Environment. = the 5 key learnings from my time at Deliverr that I will always remember as the CHASE.