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How AI Is Making The Gig Economy More Fair And Reliable For Workers



The world’s workforce faced a massive upheaval the moment Uber came on the scene. Uber was not the creator of the gig economy, the gig economy had existed for as long as we can remember, but it did signify the “mainstreaming of gigs”. 

Uber’s disruption of the transportation industry was powerful not because it got drivers to do gigs, that was already possible. It was powerful because of its powerful use of AI and technology to connect random drivers with the riders via their powerful app. This signified the first most publicized foray of AI into the industry and it quickly became the norm. 

The kick in the gut for ride-hailing giants like Uber and Lyft came when many drivers started treating the job as less of a gig and more of a full-time job. Uber had wanted people to use their services to earn a little money by the side, but their drivers soon realized that driving 80 hours or more a week, often gave them a better income than their day jobs. 

People started working for ride-hailing companies full time and ditching their jobs.   With full-time work, comes the expectations of full-time benefits, something Uber and co were adamant not to give. When cases of assaults, sudden unexplained de-activation of accounts, and a consistent slash in incomes became rampant, drivers began demanding full-time benefits and a change in their recognition from independent contractors to employees. In many ways, these fights are still ongoing despite Uber’s attempts at pacifying the drivers 

The battle between ride-hailing companies and their drivers underlines the problems at the heart of the gig-economy with the infiltration of AI. As companies continue to utilize gig workers, they continue to exploit these workers because of their “invisibility”, temporariness and their perceived inability to unionize. 

One sad conversation with a driver trapped in this broken ride-hailing system was enough to spur Firdosh Sheikh into starting DRIFE, a ride-hailing company that focuses on delivering a more equal, and ethical ride-hailing experience. 

Sheikh’s strong desire to create a business around equity for these drivers led her to start developing a platform that democratizes the ride-sharing industry. The DRIFE model utilizes a powerfully advanced platform that allows drivers to make a livable income by taking 100% of the income home in exchange for a small subscription fee. Riders can also save a lot of money because of the absence of a middleman. 

“The ride-hailing debacle of the last 5 years is proof that when tech and AI are utilized without empathy, it can cripple a system that has so much potential,” says Sheikh.

“We, on the other hand, are working hard on DRIFE to show people that technology can deliver equity when used with empathy. Whatever problems technology causes, only technology can solve. This is why the gig-economy will become fairer not with less AI and tech, but with more humane, and equity-minded applications of these technologies ”

AI, And The Gig Economy

Sheikh’s sentiment is popular among the upper echelons of the gig economy. There is a growing resignation to the fact that AI has come to stay and for good reason too, the rampant rise of AI solutions for everything is startling. The solution seems to be found only in a change of perspective. 

While it is true that robots and AI-powered systems are replacing workers in the gig economy, it is also true that all the freelance platforms and the platforms that connect gig workers to employers are either already AI-powered or headed in that direction. This means that AI might be providing more jobs than it is taking. 

The gig economy might offer companies and businesses cost-efficient options to getting tasks done, but it doesn’t automatically make finding a fit easy. AI-powered platforms have begun utilizing data to help both gig workers and employers find exactly what they need. 

AI Creates The Right Fit

The ‘fit’ of a pairing is often the catalyst for more equity and fairness in working conditions. For instance, freelance writing platforms like Clearvoice have perfected their AI-platform matching to enable employers to find the best niche writers for their tasks. This is responsible for why their platform is one of the most profitable for writers. 

AI’s ability to analyze and inteprete data makes it extremely effective in finding good matches for gig-workers,and companies.

Sheik also highlights this ‘fit’ phenomenon as being one of the reasons DRIFE is set to be so successful; “If people cannot find exactly what they need and what they can afford, then there cannot be fairness in a system. In our model, for instance, a rider can identify all available drivers within a specific radius, but the drivers can send bids to the rider. This enables the rider to pick the best fit for them based on personal parameters, cost, proximity, reputation even gender. This introduces re-negotiations and consequently fairness”

AI Fills the Education Vacuum for Gig Workers

AI is also changing the very nature of certain tasks. The result of this is that many of the people who performed these tasks are no longer qualified to perform their more tech-reliant equivalent. 

These AI-inspired evolutions demand that workers in the gig economy continue to upskill and re-skill to find sustained relevance. This need is also met by the deployment of AI-powered learning which makes it easier to pick up micro and macro skills. This only goes to underline Sheikh’s point that only technology can solve the problems it brings. 

The proliferation of AI-powered Edtech companies is one reason why the participants in the gig economy are growing fast. These platforms are easy to use, very customized, and cheaper than conventional education or one-on-one learning. 

AI Is Improving The Output of Gig-Workers

The most obvious benefit that gig workers get from AI is the targeted marketing of their services via social media. However, AI is also being utilized in more relevant ways. 

AI-powered solutions that improve accuracy, check for errors and make smart suggestions to the gig-worker has become invaluable and increasingly available in every area of the gig-economy. 

For instance, Grammarly doesn’t only improve the correctness of a freelance writer’s work, it also makes personalized nudges and suggestions on how to make it better. 

Several apps are beginning to integrate smart suggestions and personalized nudges that tell the user a feature they might benefit from, or direct them to a resource that might be helpful in the execution of their task. 

Every gig worker knows that higher output means a higher ability to charge and earn more.

The Future of AI And The Gig Economy

Sheik is one voice amongst many others who voices optimism for the gig economy. 

More tools, more AI software, and more technology would be built to help the freelancer and the gig economy worker,” says Sheik.

“We are doing exactly that in the ride-hailing industry with DRIFE and many other brilliant entrepreneurs are doing the same in other industries. I think the future of this relationship between AI and gigs is in the creation of more beneficial tools”

The Future is AI-powered. In today’s world, data is king and the ability to understand and manipulate data will give anyone an edge. The gig economy like every other industry will have to evolve.

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Gig Worker Benefits Platform Stride Health Announces $47 Million In New Funding




Stride Health, a benefits platform designed specifically for independent workers, today announced that it has raised $47 million to build on its platform, grow membership, and expand partnerships and distribution channels. 

The company helps independent workers—freelancers, part-time workers, independent contractors, and other gig economy workers who don’t get health insurance benefits through an employer—sign up for health insurance via It guides users through health plan selection and offers members other financial benefits and guidance. 

“The reason we exist, what excites me and gets me out of bed every day is that we need an individualized benefits system that draws affordability, portability, and access,” said Noah Lang, Stride cofounder and CEO. “That’s why we’re here.”

To date, Stride has enrolled 2.7 million members. To reach independent workers, Stride partners with companies that rely heavily on gig workers, such as Uber, Amazon, DoorDash, Instacart, and GrubHub, among others.

This year, Stride increased health insurance enrollments 3.5 times over 2020, highlighting the opportunity to serve gig workers with benefits traditionally provided by employers. 

While half the U.S. population gets health insurance through an employer, more than one-third of the workforce works in the gig economy full- or part-time, according to Upwork.

Covid-19 only accelerated Americans’ embrace of the gig economy. Upwork’s data also showed that 12% of workers started freelancing during the pandemic. And there may be no turning back; 60% of people who had taken up freelancing reported that no amount of money would convince them to take a traditional job again. 

But the pandemic also revealed cracks in the traditional employer benefit system, according to Lang. People who lost their jobs and took up independent work were forced to find their own benefits or go without coverage during the pandemic.

“If we had decoupled those things more constructively, most people [would] be better off,” Lang said.

The needs of independent workers will only become more central in the U.S. By 2028, an estimated 90 million Americans will be freelancers.

Freelancing and other independent work offers flexibility and earning power, but leaves these workers without the financial benefits of traditional employment. 

“While we’ve seen that kind of unbundling of work and income and benefits and safety nets, we’ve not seen an upgrade or an update to the way those benefits get delivered,” Lang said. 

The modern-day employer-sponsored health insurance system emerged in response to wage freezes during World War II and Lang says the system hasn’t kept up with changing times.

“We had this 70-year-old benefit system that has not evolved one bit,” he said. “While at the same time, work has changed dramatically.”

Investors clearly see the business opportunity in redesigning employee benefits for workers outside of traditional full-time employment. 

“The speed at which Stride’s business is scaling speaks to the urgency of the need and the value that its platform delivers to this essential, yet underserved, segment of the U.S. economy,” said Megan Guy, General Partner and Co-Founder of King River Capital, in a press release. 

Guy will join the Stride Board of Directors, along with Opeyemi Oluwole, senior vice president of Consumer Engagement at Teladoc, bringing the number of women on the Board to two. Like nearly half of all venture-backed healthcare companies, Stride previously had no women on the Board.

The latest Series C funding, led by King River Capital along with Mastercard and Allstate, brings the company’s total fundraising to $96 million. Previous investors include Venrock, NEA, Fidelity’s F-Prime Capital, and Moderne Ventures.

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Pacific Prime Dubai wins AXA-GIG’s “SME Rising Star” award in 2021




DUBAI, United Arab Emirates–()–Pacific Prime Dubai, a global health insurance brokerage and employee benefits specialist, is extremely delighted to announce that they have been presented with AXA-GIG’s SME Rising Star award at the insurer’s annual broker event at the French Pavilion Expo in Dubai on 17 October, 2021.

Working with SMEs in a range of industries, Pacific Prime Dubai has a nuanced understanding of the challenges faced by SMEs, and has expertise in helping SMEs find the right insurance solutions at a competitive price point. The brokerage utilizes a tailored, technology-driven approach, which includes their bespoke Prime Care Portal (PCP) to simplify the entire plan administration process.

Laura Gerstein, Chief Employee Benefits Officer at AXA-GIG, said: “During our 2021 VIP Broker event at EXPO 2020 French Pavilion, we were delighted to recognize Pacific Prime with our Rising Star – SME award 2021. This award reflects the substantial growth of SME group business policies that have been placed over the past 12 months. May we continue to collectively grow our businesses together to benefit our mutual clients and members with the best products and services in the MEA region. On behalf of the entire AXA Gulf Employee Benefits Team, thank you!”

David Hayes, Regional CEO at Pacific Prime Dubai, said: “I would like to extend a huge congratulations to everyone on the team for this well-deserved award. This is the second year in a row that Pacific Prime Dubai has received an SME-based award from AXA-GIG, and I believe it is a testament not only to our strengths in servicing SME clients, but also our long-standing partnership with AXA-GIG.”

About Pacific Prime Dubai

Established in 2000 in Hong Kong, Pacific Prime is a global health insurance brokerage and employee benefits specialist, focusing on delivering best-value insurance solutions to individual and corporate clients around the world. The brokerage has grown to establish a truly global footprint with a presence across Asia, the Middle East, Europe, and the Americas.

To learn more about Pacific Prime Dubai, please visit:


AXA is one of the world’s leading insurance and asset management groups, servicing individuals and business clients in 54 countries, while GIG (Gulf Insurance Group) is the regional anchor to AXA’s global expertise. This comes after GIG completes an acquisition deal for AXA operations in the gulf region.

To learn more about AXA-GIG, please visit:

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Baskett weaves rookie season into starting gig with hometown Wanderers




With the HFX Wanderers’ offence sputtering recently, young keeper Kieran Baskett has become the Canadian Premier League club’s de facto MVP.

But for the rookie from Halifax, he’s just doing his job for the hometown team in the thick of a playoff hunt.

I’d like to see us score more goals but that’s not my problem. I’m just happy to do my job and if we’re scoring goals or we’re not, I’ll do my best to keep the ball out of the net.

“My job is to keep the ball out the net and I try to do my job as best as I can,” said Baskett, who turned 20 on Sept. 27.

“I’d like to see us score more goals but that’s not my problem. I’m just happy to do my job and if we’re scoring goals or we’re not, I’ll do my best to keep the ball out of the net.

“The main thing is we’re not getting beaten and that’s a really good quality to have going into playoffs. I think we’re a hard team to beat.”

While the offence has sputtered recently without injured scoring star Joao Morelli and his league-leading 14 goals, the Wanderers (8-7-10) have held onto the fourth and final playoff spot in the CPL table. (They remain one point ahead of York United with three games remaining in the regular season.)

In their past four matches, the Wanderers have been shut out in three of them and in the other – a 1-0 victory over Pacific FC on Oct. 11 – the lone score came on a Pacific own goal.

As a team, the Wanderers have scored a league-low 26 goals. Yet, in the past two months, they are the hottest team in the CPL with only one loss in 14 matches since Aug. 14. Eight of those results, though, were draws.

Baskett has posted three clean sheets in a row, beginning with the Thanksgiving win over Pacific and highlighted by a spectacular save in the final minute of stoppage time Oct. 17 in Calgary. Host Cavalry FC was awarded a penalty kick, but Baskett made an unbelievable stop, diving to his right to deny lethal striker Joe Mason with his fingertips to preserve the 0-0 draw.

Since Sept. 6, Baskett has started in eight of the Wanderers’ past nine matches, posting a 4-1-3 mark, and their Canadian Championship quarter-final against CF Montreal on Sept. 22.

HFX Wanderers keeper Kieran Baskett dives to make a save during an Oct. 6 match against Forge FC at the Wanderers Grounds. - TREVOR MacMILLAN / CANADIAN PREMIER LEAGUE
HFX Wanderers keeper Kieran Baskett dives to make a save during an Oct. 6 match against Forge FC at the Wanderers Grounds. – TREVOR MacMILLAN / CANADIAN PREMIER LEAGUE

What’s impressive is that Baskett’s debut didn’t come until Aug. 17, when he got the start in the Wanderers’ Canadian Championship preliminary match against AS Blainville, leading the Wanderers to a 2-1 victory.

“I didn’t see it working out like this, but I always thought I’d get my chance,” said the six-foot-three Baskett, who joined fellow Haligonian Christian Oxner to form the Wanderers’ goalkeeping tandem for the 2021 season.

“I have definitely been fortunate with how it has gone. I think I’m doing what I can to keep the job. It’s been a great season for me. I’ve learned a lot and I’ve improved in the last two months, just playing the games. I’m up to speed at this level.”

It has happened at a lightning-quick pace. But if it wasn’t for the COVID-19 pandemic, Baskett would likely still be studying and playing NCAA Division 1 soccer at the College of William & Mary in Williamsburg, Va.

The former Suburban FC keeper – whose mother, Gillian Hamilton, competed for Canada in the biathlon at the 1994 Winter Olympics – attended boarding school in Maryland and played for Baltimore Celtic Soccer Club while in high school.

His freshman season at William & Mary in 2019, Baskett started all 18 matches and played every minute in goal for the Tribe, leading the Colonial Athletic Association conference in saves (71).

Then the pandemic hit and shuttered the 2020 season. Baskett didn’t return to the States, opting to do online learning. It was in January when the Wanderers offered him a contract for the 2021 season with a club option for 2022.

HFX Wanderers keeper Kieran Baskett leaps to grab the ball to deny a scoring attempt by AS Blainville during a Canadian Championship preliminary match Aug. 17 at the Wanderers Grounds. - TREVOR MacMILLAN / CANADIAN PREMIER LEAGUE
HFX Wanderers keeper Kieran Baskett leaps to grab the ball to deny a scoring attempt by AS Blainville during a Canadian Championship preliminary match Aug. 17 at the Wanderers Grounds. – TREVOR MacMILLAN / CANADIAN PREMIER LEAGUE

An opportunity to stay home and play pro soccer couldn’t be turned down.

“Things happen for a reason,” said Baskett, who’s still pursuing his education by taking online classes at Dalhousie. “It was good timing for me, just a blessing. The pandemic brought me back home, but it allowed me to pursue my dream as a professional.

“My parents were a little concerned about me leaving university. But I always wanted to play professional soccer. I never thought it would be in Halifax.

“It’s definitely a big step up from university. The ball moves faster at this level and the shots come harder. It took some time to get used to.”

The Wanderers head out on their final road trip of the regular season. They travel to Winnipeg to face Valour FC on Tuesday evening and then to Hamilton to play Forge FC on Saturday. The Wanderers’ regular-season finale is Nov. 7 at home against Atletico Ottawa.

“We have to get the results,” Baskett said. “If we can continue what we’re doing defensively, I think the goals will come. We’re in a pretty good position heading out on the road.”

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