Getting in touch with my former persona, as a startup founder

Gary Liu
Gary Liu

Building a startup requires a multitude of disciplines and sometimes even personas, often casting one against another as if you were on the verge of having multiple personality disorder. I feel this every single day, as the number of hats that I am required to wear has accumulated into a pretty neat collection (I actually never wear hats in real life as they make my head look funny). In many ways, I feel lucky to have gained the breadth of experience in both designing and selling digital SaaS products to all sorts of customers, and you wouldn’t believe how experience seems to always make sense of everything, at the end of a long day.

Cradle has come a long way since we first sought out to change how businesses talked to their customers back in late 2016. Time certainly has a way of expediting itself while you’re having a blast doing something that you love. In the past 18 months, my role has shifted from designing all aspects of Cradle’s product lineup and brand to now, cold sourcing prospects to get our foot into their door. The shift was gradual, as the design requirement became less urgent and abundant, and truthfully, I wasn’t looking forward to the day where my daily routine would change from designing beautiful modals to facing rejection 9/10 times. Well that day came and it came with an unsurprisingly rude awakening, when we had cemented our main goal for 2018 — SALES!

If it’s on the wall then it must be real

Most of my friends and past colleagues in SF may still remember me as “crazy, sales Gary” because it’s rather difficult to shed your former persona, which made you a caricature of your work — building sales teams from scratch that helped the companies that I worked for reach a couple key milestones. But here I was, in the early days of 2018, staring at our KPIs for the rest of this year and knowing how critical these sales numbers would have on Cradle’s future trajectory.

I took a deep Ujjayi breath (I am a devoted Ashtanga yogi) and tried my best to rediscover the fiery, wall-breaking, and relentless drive that helped push myself to places that I never thought I could ever reach. To my surprise it didn’t take long for me to rekindle that energy because it had never left me in the first place. Rather, I had learned ways to contain it and then channel it in a healthy, sustainable way (like yoga). It was time for me to step up and so I did, with a long exhale.

So where the hell do I even begin?

One of the first and hardest challenges of crafting an initial sales process is figuring out in which outbound channel to test your initial sales pitch. Should I send out cold emails to potential decision makers? Knock on doors? Call the office manager directly? After getting advice from some former colleagues and blogs, I opted to give Linkedin Sales Navigator a try. I signed up for their 30 day free trial (always a good bet) and went to town.

Some context to my initial outreach strategy. We have been working with Rightway, a prominent accounting firm in NZ, to help make their phone communication more engaging and seamless. In a short time frame, we were able to reduce their number of missed calls by 80% which meant that many of their valued customers were able to be helped by a live person rather than dealing with the dreaded “you have reached the voicemail of…”. Through the course of our partnership, we have gotten to know them quite well and they have been tremendously supportive even in the earlier days when some nasty bugs would appear out of the blue 😅.

Having Rightway’s full blessing, I decided to leverage our blog post and my connection (or lack thereof, initially) in the accounting industry in NZ, to help me connect to other accounting professionals that may have similar pain points. So I started sending out a quick intros through the “connect” functionality (tip: there’s no limit to the number of people you can friend request but there is for InMail). So here’s my generic, yet customized intro where I try to build a bridge through mutual connections, whilst introducing my reason for the outreach:

I have had good success with this method thus far as most of my metrics are inline with my initial projection.

100 requested > 20 accepted request > 6 Responded (the other 14 required additional nudging)

For the most part people have been fairly positive and direct which is more than I could ask for, as I am cold calling them after all. Then I got this message:

Fair enough. Some people are not authorized to give out certain information (even though most of it is public nowadays, such as the head of a department). But I wanted to know why he was so hesitant in his response, as it may help me find a better way to engage with others in the future.

I tried to use humor to alleviate some of the tension but I wasn’t able to win this prospect over.

Yikes. I didn’t anticipate this much aversion to something that I had thought was purely harmless and even intriguing, in my honest opinion.

Successful sales outreach relies more on the process than just charisma

But having good charisma definitely helps, if your process can help you reach the right decision maker. In my conversation with the gentleman aforementioned, I had thought my value proposition was enough to garner his interest and/or even his willingness to direct me to the right decision maker. Clearly, it frustrated him that I had used Linkedin for sales prospecting but in an age of constant distraction, including but not limited to, social media, click bait news, emails and red notification alerts, I still believe that it’s not the medium but the content itself, that will ultimately captivate and be worthy of one’s attention.

Knowing this, I decided to brush off this minor incident aside and continue the task at hand. After a few more weeks, I was able to gather more data around my outreach effort.

100 requested > 20 accepted request > 6 Responded (the other 14 required additional nudging) > 3 Quick Chat > 2 Trials > 1 Customer

So in essence, I had a success rate of 1% from cold Linkedin requests to a paying customer. Not the worst but there’s definitely room for improvement, both in the iterative process of developing more effective messaging, but also in ways of making the outreach process more scalable.

Strangers can often surprise you

One of my takeaways from this exercise has been that a good number of strangers are more than willing to help you out than you would give them credit for. Sure, a vast majority of people simply ignored my request but the ones who responded showed a great deal of compassion and candor.

As we continue to test out new ways to improve our outbound sales metrics, I will always remember this:

Be kind to people on the way up — you’ll meet them again on your way down. — Jimmy Durante
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