When I opted to be salesguy in my 40s

Last year in November, I asked for a sales role after failing to relate to the Operation profile outlined to me. I am 45 years old without any sales experience and was sure to be refused. But, my hiring manager was an ex-colleague from the Company we worked together (2008–2011) who surprisingly agreed and said, “We let you romance the idea of being a salesperson.’

Hence, I start my third career transition from strategy-to-finance-to-Operations-to-sales in 18 years of my work life. Sales role was going to be challenging for the following reasons:

a. No first-hand sales experience

b. Technology intensive product with 4–6 months sales cycle

c. Poor networking skills

I was ready to take up the challenge backed by the belief that ‘Sales’ is science rather than ‘art’ and sticking to a well-defined process and being persistent will give me the results I aimed for.

November 2020:

• I was onboarded remotely
• My request for co-working space approved
• I choose a strict 9 to 5 routine at the co-working place despite having the flexibility to work from anywhere
• Networking was never a priority; forget about the need for cold outreach to strangers. And, this was my greatest challenge and also the first logical step to be successful.
• Most of the days, I had no phone calls or emails from anyone in the Company. I had no scheduled meetings and my to-do list mostly read: prospecting, reading, and drafting email pitches.

December 2020:

• Boredom setting in
• Holiday season
• Was asked to be patient
• Spent 4–5 hours on LinkedIn and LinkedIn Sales Navigator
• Signed up for some free newsletters and google alerts
• Updated my LinkedIn profile
• By mid-December, I was back home by lunch. I cycled to the co-working place and clicked pics en route. I experienced ‘slowness’ unlike my high-engagement jobs earlier. Auto email responses from my prospects kept me hopeful of getting a response when they are back in the office, strangely though an

January 2021:

• Decided to give up the co-working space
• An office chair and a desk were purchased for WFH
• Learnt using Sales CRM, Microsoft Dynamics
• I customized the pitch deck and sent personalized emails to prospects. After sending 100 odd emails, I learned that a follow-up email was also needed. And, maybe a third one too. I was highly skeptical of advice asking for 6–7 follow-ups before expecting the first response.
• I was sending 10–12 emails each taking minimum of 15 minutes with the split of time for four activities executed sequentially as outlined below:

a. Checking the LinkedIn profile to find a talking point (6–7 minutes)

b. Searching for email id from Lusha (2–3 minutes)

c. Creating contact on the Sales CRM (1–2 minutes)

d. Drafting the email 4–5 sentences in each of the two paragraphs (6–7 minutes)

February 2021:

• My valentine (my prospects) were nowhere in sight
• Secured a meeting with the Procurement Head of an existing client
• Planned for a virtual roundtable and onboarded a vendor to execute it
• I continued with cold outreach using Inmail (LinkedIn) and email but turned hinky about the process I believed was fool-proof in January. I tended to ‘volume’ over ‘quality’ and decided to focus on sending twice the no of emails than in January.
• Planned to try our email campaign tool and tried a few on a trial basis.

March 2021:

• First change in my focus from the leadership. I am asked to singly focus on pitching the MLOps platform (product) alone instead of pitching solutions.
• 5–6 customers for POC was the target I had to work towards. The leadership hoped for 5–6 POCs by end of the 2021 but I preferred to keep a stricter timeline and hoped to win 5 POCs well before September.
• It was a new start as pitching a product is much easier compared to pitching Solutions-as-services to enterprises. I was given the liberty to pitch to customers of any size and any industry.
• The first roundtable was executed successfully and I had 4–5 prospects to talk to and request demos. I had the first demo scheduled for April first week. I thought the days of cold outreach were a waste of time and instead a smartly organized event is more effective.

April 2021:

• Signed up for 5 roundtables/webinars with the event’s vendor
• 1 POC signed (4 left)
• Planned to target South Africa as the target market
• By the first week of April, I had 3 more meetings planned for the remaining days of April. I felt engaged a little and motivated to keep trying new approaches to prospecting.
• The subscription and google alerts of my target companies gave me the first prospect to pitch. I read the article published and then pitched it to the head of the company.
• He replied to my second follow-up email by forwarding it to his senior leadership to discuss further. And, here comes the second demo and a follow-up meeting happening for the same customer in quick succession.

May 2021:

• 12 prospects generated
• 1 POC signed (3 left)
• I felt like cracking the code of getting customers
• My target of 5–6 POCs was likely to be accomplished earlier than September
• The first event for South Africa was conducted but failed to make any significant inroads into the market. But, I was sure of having a couple of customers from there for the POC and a couple of the South Asian market from the podcast that was launched in alliance with a reputed podcast host.
• The first mistake that I committed in May and realized later in September was this: I stopped focusing on cold outreach for new prospects. I believed a chain will follow and similar companies will soon ask for a demo and maybe I can just stick to tracking alerts and pick my next target prospect. I wrong.

June 2021:

• 7 prospects generated; none reached the POC stage
• 1 POC from previous months prospects signed (2 left)
• Marketing qualified leads did not come through as planned
• I was anxious the no of prospects fell compared to May month. The approach to drive engagement from LinkedIn posts and outreach was not materializing. I inadvertently concentrated too much on India and South Africa. The process of profile visits and building some traction with prospects in the US was missed out completely.

July 2021:

• Only two prospects from the roundtable conducted for South African customers
• Both dropped
• I was losing the momentum and failed to get the response I had witnessed in the previous two months. Prospecting alone and singly won’t get the scale that I was working towards. The marketing team decided to limit the spending to a minimum as failed to match up the traction benchmarks outlined.
• Despite the feedback from the customers about the platform that I was pitching, I stuck to the belief that despite all feedback, I will continue to believe that the platform is saleable had I done a better job at prospecting.

August 2021:

• 5 customer prospects
• 1 POC signed (1 left)
• Asked to focus on signing up partners for the platform and limit the focus to the US market
• I was unhappy with the decision but as a newbie, I could not claim to know the market and sales process better than who suggested me. I lost the momentum and felt like wasting my time on something that is not going to translate into anything materialistic. I did have a new project win from the existing client plus a master services agreement signed as well to tame my anxiousness.
• Left for my annual bike trip and hoped to be able to meet the remaining POC targets by December. My self-justification – Had I was not asked to limit the focus to the US market alone, I could have done better and met the targets as planned i.e. end of September.

September 2021:

• Leadership change and the company becomes 100% subsidiary of a global IT solutions and Services provider
• Literally free as the focus was not clear
• Asked to refocus on the US market both for the platform and solutions business
• Marketing qualified leads assigned to be were to be converted into sales qualified leads
• No closure happened.

October 2021:

• Assigned the Account Management responsibility for the Parent company
• In a year since joining, my role transitioned from a salesperson whose success was contingent on prospecting for new customers to managing relationships with the parent company for new business.

(Posted on my LinkedIn profile as well)