Listen to the first chapter of Cyphers & Sighs – available on Audible, Kindle, and in Print on Amazon
What happens next is an action-packed thrill ride through London, Tel Aviv, and Hong Kong
Chapter 1 – The Woman At The Bar
Ryan Harman, aiCheckmate’s Chief Revenue Officer, and his US sales team wrapped up the first day of a two-day National Sales Meeting in Chicago. Contrary to the casual attire standard among software professionals, his sales team is suited up, a preference of Harman’s. aiCheckmate is a darling of the tech world, with seventy million dollars in venture funding, and Ryan always believed in the old adage: Dress for success. He would not tolerate any black mock turtleneck, blue-jeaned, Steve Jobs wannabes on his team.
aiCheckmate’s initial AI product, Stalemate, was widely recognized as the top cyber-security software product on the market, it harnessed an AI engine to monitor all access points and elements of an organization’s systems, then recognized and immediately employedemploy countermeasures to thwart intrusion attempts.
On a cold, damp Chicago October night, the team found themselves at Pippin’s Tavern on Rush Street, letting their hair down. Eight of them, five men and three women, settle into the rhythm of the night, raising their glasses and swapping tales, each taller than the last.
“We’re celebrating Vanessa’s big win. Drinks are on her.” Joked Harman as he raised his bourbon glass for a toast. “This deal is going to open a lot of doors for everyone around the table.” Vanessa, a tall, handsome young woman, was one of Ryan’s top performers. She recently closed an eight-million-dollar deal with a three-letter agency referred to as customer X.
Vanessa Jones was a combination of Einstein and Coco Chanel, a fashionista with an MS in Electrical Engineering from MIT. She was one in a thousand engineers who could speak and relate to humans. Her territory was the District of Columbia, Maryland, and Virginia, commonly referred to as the DMV, and she worked closely with the Defense and Intelligence agencies.
Ryan met her at an MIT career day five years ago. It took a lot of determination and grit for a woman, especially a Black woman, to graduate with honors from MIT. He wanted her on his team and didn’t think he had a prayer of recruiting her, but she accepted his offer despite the fact that Ryan hadn’t prayed or stepped into a church since his marriage over a decade ago.
It wasn’t the prayer or lack thereof that attracted Vanessa. She had college loans, which thoughts and prayers wouldn’t pay off. She was motivated by the money. Ryan offered her the opportunity to work for a well-funded startup unicorn, offering a respectable salary, stock options, and the prospects of the gold and riches in the commissions she’d earn by selling the world’s most innovative cyber-security software to the most demanding, well-funded, intelligent agencies in the world.
“So, Vanessa,” Chris Long asked, “have you ordered your Gulfstream yet?”
Vanessa responded, “I’m looking at Mercedes money on this deal. The Gulfstream will have to wait till next year, Chris… Chris?” She frowned at Chris, realizing he hadn’t heard a word she said. Chris’s eyes were laser-focused on a moving target that had just entered the room. The volume in Pipin’s seemed to hush as all eyes, male and female, fixated on the exotic, raven-haired beauty who walked across the room to sit at the bar.
Vanessa’s win and the group’s chatter were put on hold as the team was treated to the live-action version of Swipe Left. One after another, potential suitors walked up to the woman and left in dejection.
Lenny Baxter, aiCheckmate’s San Francisco, West Coast rep, suggested they start a pool… Lenny was a heavy-set, jovial, fifty-six-year-old divorcee who had been carrying a bag for Silicon Valley startups since graduating from San Diego State thirty years ago. He suggested a betting pool to see how many men crashed and burned before someone was invited to sit with the woman. Baxter would bet on anything. He once proposed that Ryan and he bet if the next bird to take a crap on a car would be a pigeon or a seagull. Ryan didn’t take the bet… by the way, anyone with money on a crow would have won.
As Lenny started explaining the rules of the game, Chris, a twenty-eight-year-old, former TCU tight end, and the newbie to the team, swirled his Blanton’s, tipped his hat, donned his best, albeit questionable, John Wayne drawl, and announced, “Reckon I’ll head on down the range, make sure that little lady over yonder isn’t bothered by any more no-good varmints.”
The team giggled and teased and watched as he left the table.
Tall, with a cowboy’s stride and sandy hair contrasting with his dark suit and cowboy boots, Chris boldly approached the mysterious beauty.
From their vantage point, the aiCheckmate squad watched with bated breath, trading suppressed chuckles as Chris joined the singed pile of failed suitors. He returned to the table, and Ex-Marine Dexter “Dex” Johnson quipped, “Dang shame how she wounded you, Chris. Do I need to call a medic? Let me check you for a pulse..”
Dex was a Naval Academy grad who did his time in Afghanistan. He loved the Corps, his comrades, and the brotherhood. Yet one day, after a particularly trying mission, he calculated he wasn’t earning enough dollars per bullet aimed his way. He concluded he could live longer, eat better, and make more dollars per bullet in a career where people weren’t aiming to shoot him. Dex joined the aiCheckmate team two years ago, lived in Boston, and his territory was New England. Ryan admired him and respected him. They were both developing a trusted relationship.
Everyone laughed at Dex’s comment. Everyone but Chris. Slightly defeated, Chris probed, “What’s so funny?”
“Your flameout, Cowboy!” chided Dex.
“The lady’s a foreigner, and I don’t think she likes tall, handsome Texans,” Chris replied defensively.
Carla, the articulate Columbia grad from the company’s NYC office, retorted, “Chris, you wilted quicker than a snowflake in the Texan sun.”
“Let’s see you do better, Carla.”
“Sorry Ryan, my hubby wouldn’t approve, or on second thought, maybe he would. But I don’t roll that way, not that there’s anything wrong with rolling any way you choose.”
Carla Pushkin had a special place in Ryan’s heart. She had tremendous EQ, a valuable skill for a salesperson. Her customers loved her. He poached her from Oracle, where they worked together in a prior life. Her territory was New Jersey, New York, Pennsylvania, and Connecticut. Like Vanessa, she was over-educated for her role. Carla was married to Mark, a prominent New York City eye surgeon, and she spent most evenings pursuing a graduate degree in psychology. Money wasn’t her primary motivator, and Ryan knew he’d lose her when she earned her MS.
During joint sales calls, Carla enrolled Ryan in Mrs. Pushkin’s Finishing School. She rounded out Chris’s rough Jersey-Bro edges by teaching him obscure etiquette lessons like, “When a revolving door is stationary, the woman goes first; when it’s not rotating, the man goes first to start it moving,” and “on escalators, the man goes first so as not to compromise the ladies’ posterior.”
Amidst the gaiety, Chris issued a challenge, “Alright, Ryan, if you’re such a stud muffin, how about you show us how it’s done, boss man.”
Ryan raised his hands in mock surrender, ” I haven’t been on the prowl for eighteen years, and bar chatter wasn’t my forte back then. What do I say to her? Something corny, like, haven’t I seen you someplace before? Or come here often?” Despite his protests, the crew wouldn’t let him off the hook. Peer pressure, he thought, was like WiFi – you don’t see it, but when you’re connected to a bad network, the signals are all too clear.
Drawing a deep breath, Harman approached her. For a brief second, he was lost in the depths of her captivating hazel eyes. Mustering up his courage, he teased her with the first thing that came to mind: “Buy me a drink.”
She arched an eyebrow, “Isn’t it the other way around? Aren’t you supposed to buy me a drink?”
Ryan noticed a slight Eastern European accent, then grinned, and relying on the quick-thinking improvisation skills that had served him so well in business, he responded, “I wouldn’t want to do that to you.
“Do what?” She asked with a curious smile.
“Well, If I buy you a drink, we’d chat and laugh; I’m funny and a likable guy; I’d buy you another drink, we’d laugh some more, and after a few more rounds, I’d ask you to join me in my room up at the Drake; you’ll be a little drunk, you’d feel tipsy and obligated, I wouldn’t want to put you in that position.”
She playfully narrowed her eyes, “Alright, cowboy. I’ll buy you a drink.”
Now Ryan’s smile turned devilish as he figured out what to say next, “No, forget it. I don’t want your drink.”
“Wait, what? What now?”
And he calmly explained, “You see, you’ll buy me a drink, we’ll laugh, have another drink, and pretty soon…
He was cut off as she grabbed him by the tie and pulled him until they were nose to nose. “Your move, funny boy.”
Before Ryan could say another word, a rush of familiarity washed over him. The petite and feisty Carla was by his side, planting a peck on his cheek. “Honey, we need to get home. We only have the babysitter till eleven.” The statement, though a playful jest, served as a stark reminder. Ryan’s thoughts immediately drifted to Phoebe, his ten-year-old daughter. The evening’s escapade might have to wait for another lifetime.
As they walked away, Carla said to him, “You looked like you needed some help there.”
He looked into Carla’s warm brown eyes, took a moment, and said, “Thank you for bailing me out. I had no idea how I was going to exit that gracefully.”
Carla smiled and replied, “I knew you weren’t going home with her. That’s not who you are.”
Ryan wasn’t so sure about that as he thought, “I didn’t enter that little chit-chat thinking it would lead anywhere… but that was close to the first time I ever thought I might cheat on Amy. Who knows where it would have gone if Carla hadn’t pulled my ass out of the fire. ”
The moment the aiCheckmate team left Pippin’s, a beautiful raven-haired temptress, seated at the bar, removed her mobile phone from her purse, dialed an international number, and said, “Almost, but not yet. I’ll try again later tonight.”
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