Photo by Matheus Bertelli
Bob and Alice - Anti-Design Patterns in Life, Love and Tech will soon be a book. Join other smart people who absolutely love Bob and Alice today.
👉 If you enjoy reading this post, feel free to share it with friends! Or feel free to click the ❤️ button on this post so more people can discover Bob and Alice. 🙏
Venice 6:00 AM
Sol was the fifth daughter of musical hippie parents from Haight-Ashbury. Sol was a cheerful, high energy crossfit trainer. I was in Sol’s 6:00 crossfit class in the Venice gym. By 7:00, psychopath Sol had taken us to the edge and finished us off.
Today, Barry and I were taking the United shuttle to SJO for a 1030 face-to-face meeting with the city of Sunnyvale. The sales cycle was stuck in an endless, aimless spiral of good meetings with HR and payroll people. Rumor was that we had already lost the deal to EY.
I needed to clear my mind before Barry picked me up to go to LAX.
I sat down on a mat in a lotus position and started tonglen breath meditation.
Breathing in Alice’s pain, breathing out compassion. In a few minutes, I was in another place. Visualizing myself in front of the ocean. Visualizing Alice and Sunnyvale far away in the distance behind me. Breathing out my compassion to people with pain like me.
Early morning light streamed down the warm walls in shimmering lemon torrents, touching the gym equipment that responded with a bluish-gold reflection.
Alice walked in with her gym bag. She had a court appearance downtown, prosecuting a couple of low-level Columbians for money-laundering in connection with Hezbollah.
She looks left. Sees me in a lotus position, eyes closed, breathing slowly in and out. Taps me on my shoulder.
Alice, “Hey”.
I get up, “Hey”.
We look at each other.
Alice improvs a haiku for us -
Close beside him now,
His scent, a tangible truth—
Is his love as real?
LAX to SJO
Barry parks and we take the shuttle to Terminal 7 to United Express.
The terminal is a zoo full of passengers and security screening checkpoints manned by minimum wage TSA workers. An unmatched spectacle of massive audience-participation security theater.
Two older women are in line in front of us with Trader Joe reusable canvas bags in each hand. They are negotiating with a TSA worker.
Woman #1, “My friend Clara is allergic to magnetometers. The magnetic field you know is very dangerous to you and it gives Clara terrible headaches”. The TSA worker calls her supervisor and after a brief discussion, sends Clara with a lady TSA worker for a pat-down outside the line.
I say to Barry, “Barry, you know that this is a perfect opportunity for her friend to remotely-detonate Clara. They could kill 150 people and shut down LAX and West Coast air traffic for the day”.
Barry, “Keep your voice down man. You’re spending too much time with Pesya”.
Pesya, matron of the Silicon Valley hackers, is their cybersecurity expert. Pesya sees exploits where other people see buildings, doors and windows. Thinking about joining a gym and losing weight. More interested in finding zero-days.
They land in San Jose on time.
Barry’s phone buzzes.
It’s Madison - their contract sales rep for Northern California. Madison works out of a WeWork in Sunnyvale.
Madison, “I see you guys. Look to your left. I’m in the cherry-red Toyota Tacoma”.
Madison is a formidable Australian gal who relocated to California to find her fortune. Cheeky and high-energy.
They get into the truck.
I ask Madison, “I love your truck, what’s the story?”.
Madison, “Last Monday was my birthday. Business is good. I wanted to treat myself. I deserve it. The dealer said the wait time is 2 months. So - I said, f-k man, but today is my birthday, I need this truck today. I’m buying it today - in cherry-red. I’m not leaving without the truck. The salesman made some calls and they found one at another Toyota dealership. While they brought it over, we did the paperwork. So here we are”.
Madison gets on the 101 North and merges into traffic, and in between phone calls, she updates us with the latest status of the deal with the city of Sunnyvale.
Barry, “Madison, what are all these calls?”
Madison, “I have another gig. I sell food packages online to expat Australians in the US. After I moved here 2 years ago, I got homesick for Vegemite and Tim-Tam and figured that there was a market for iconic Australian foods”.
Barry, “Very cool, so what is your assessment of the deal right now?”
Madison, “Well you know, we got an incoming lead just after the press release of our win with the City of San Jose. I called them back within 15’ of the contact form hitting our CRM. It looked very promising. The problem is that our contacts there are mid-level HR and payroll people. They don’t have the power to decide, but they have the power to say no.
I’m friendly with the payroll manager, Hilda. We had lunch last week. Hilda says that EY won the deal.
I think they used us to build their technical specifications and get pricing.
I wanted to talk to the CFO, but I was afraid that if I bypassed HR, I would alienate my contacts and burn the deal.
I want this deal so I ran with my inbound lead ”.
Barry, “Yeah, well, don’t feel bad about feeling bad.
We still have a few tricks in our bag, like bringing in Pesya and scaring the crap out of them over cyber and CCPA (California Privacy) Compliance.
EY can bundle gig worker time collection into their master service agreement for IT outsourcing, but no way the suits from EY can compete with our security and technology platform”.
They get off at Mathilda Ave and arrive early, 15’ before the meeting.
Madison parks and Barry calls a 5’ huddle outside before the meeting.
Barry, “What we do is listen. Madison will make the introductions, let’s go”.
Barry is Italian mafia chic, charcoal gray suit, crisp light blue dress shirt, silk tie, dark brown loafers and Breitling.
I’m in my role as the Silicon Valley CTO (Chief Technology Officer) . Giganet-branded T-shirt, well-fitting chinos and Allbirds, wearing my Suunto Vertical watch.
Madison is in role of the Gen Z Australian sales rep opts for a smart-casual ensemble. Electric blue blazer over a red blouse paired with gray high-waisted trousers and stylish flats.
We’re escorted into a conference room with Mary the head of HR and Hilda head of payroll.
I’m thinking, bad sign, too few people at the meeting. This can’t be good news.
Madison does the introductions.
Mary starts, “I’d like to thank you all for coming in today. Madison has done a great job of presenting your value proposition to help us reduce costs, improve compliance and process gig worker payroll.
But - I’m afraid that we have some bad news.
Our CFO is leading a reorganization. Changes are happening quickly, and several people in the accounting, HR and payroll departments are now looking for new opportunities.
We have to get through this organizational change before considering new technologies”.
Madison decides to be cheeky. “So you’re saying, your CFO is shaking bushes and people leaving?”
Mary unfazed, “Yes, Madison. We’re in a state of flux right now”.
Barry raises his hand. “Ma’am, can I ask you a question?”
Mary, curious at Barry’s Italian politeness, smiles, “Of course, Barry”.
Barry smiles back, “Can you introduce us to your CFO?”.
Mary smiles at Barry, “Of course, it would be my pleasure to do that. Let’s walk over to his office and say hello”.
Mary walks with Barry down the hall and introduces Barry to Jack, the CFO.
They set a time for lunch and exchange cards.
Hilda escorts the Giganet team out of the building.
Madison is direct, “Hilda, How is it we are only meeting your CFO now?”
Hilda smiles, “You never asked”.
Barry and Iris have lunch with Jack the following week at his favorite Mexican restaurant in San Francisco.
Jack the CFO talks finance with Iris the CFO. Iris shows how the Giganet SaaS solution fits Jack's reorganization plan like a glove and makes Jack look good.
Iris asks Jack if his IT manager would like to meet number 1 in the world on browser security - Pesya Eichbaum.
Pesya meets the IT manager. They talk about cybersecurity and privacy trends and reducing IT workloads with native cloud platforms. Never specifically mentioning Giganet. The IT manager enjoyed meeting a Valley legend and how taking gig worker privacy off his plate makes him look good.
3 weeks after lunch with Jack the CFO, Barry strikes a deal.
Those who are victorious plan effectively and change decisively.
Sell Low
Barry and I debriefed the Sunnyvale deal, to see what we did right and where we went wrong. This is what we came up with.
In classic sales process, you start with a lead, qualify, build rapport, construct a business case and close a sale.
This may be true for buying and selling dishwashers but it’s not true in technology sales.
In a world where corporate politics flourish even in the smallest company, knowing who authorizes the purchase order is a major key to selling technology.
Proving return on investment on your solution is not enough
In fact:
Return on investment does not sign checks
Helping end-users with your software does not sign checks
Unless your offer has emotional and political benefits for a buyer, they won't sign a check. The CFO has a stack of offers on her desk with ROI without budget to buy.
The first mistake most technology salespeople make is calling too low in an organizational chart.
Salespeople get intimidated selling to the highest level because of the fear of rejection brought on by their inability to frame a strong enough sales value proposition for a senior manager. Account managers usually push to get into a targeted company, and accept any entry point to get traction.
This is always the wrong move.
Let me repeat that. This is ALWAYS the wrong move.
If you are a sales manager in a technology company, focus on having all of your sales account managers cold call ONLY VPs and above.
Remember, no matter how big the company is, managers and directors are nice people, but they almost never have the authority to sign off on business proposals.
Even when they tell you it is their decision, they are still going to go ask their boss.
Another fact in technology sales is that managers never send you up to their boss, only down to their subordinates.
When was the last time a Director of IT or Operations said to you,
“Bob, I am going to introduce you to my boss, the VP.”
It doesn’t happen. Either they bring your opportunity directly to their boss and try to make themselves look good, or they send you to George, the Program Manager. Either way, you lose.
The Director is not as good a salesperson as you are, and will likely communicate your message in the wrong way to the VP. Worse, you are stuck with George, who cannot make any decisions.
The solution is always sell up – the higher, the better.
On a park bench in Venice CA
Alice has a dream. She dreams she is sitting on a park bench with a tall, lanky bald man in his 60s.
The tall bald man was the one who began. He has a friendly, warm, and caring demeanor.
He introduces himself, “My name is Mark”.
She replies, “I am Alice”.
Alice feels secure and comfortable with Mark, like they were old friends.
Mark, “Alice, how are you? What’s new at the Bureau and with Bob?”.
The tall bald man remained silent as they sat on the park bench.
In front of them there was the green calm of the park.
A woman hungry for answers, must stock up on patience.
A man in possession of analytical skills needs to listen.
That is why Mark remained silent.
Mark listened carefully to Alice.
Alice, “FBI is good. I put away 2 bad guys today. I saw Bob this morning”.
Mark smiled and asked, “Nice - how was it?”.
Alice, “I shared a haiku with Bob”.
Close beside him now,
His scent, a tangible truth—
Is his love as real?
Alice trusts Mark and asks, “What should I do?”
And she wakes up before Mark can answer.