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Empowering Black Travel Entrepreneurs: Embracing Automation For Business Growth And Unforgettable Journeys With SquadTrip

In various spheres, from trade expos to high-level managerial positions, Black Americans remain significantly underrepresented in travel and tourism. Research indicates that only 7.2% of U.S. Travel agents identify as Black or African American, and an overwhelming 62% of travel advisers function as independent contractors, lacking the necessary tools and resources to compete with larger agencies.

Pioneering tech visionaries Darrien Watson and Stevon Judd are instigating a paradigm shift within the travel industry through a bespoke SaaS (Software as a Service) platform designed for group trip organizers and travelers. Beyond mere financial growth, SquadTrip is deeply committed to empowering 50,000 Black travel professionals over the next two years, aiming to bridge the diversity gap within the travel and tourism space. With its mission to foster community and meaningful connections through travel experiences, the software firm will share optimal strategies and educational resources via webinars, conferences, and workshops.

Watson, CEO and co-founder of SquadTrip, highlights, "One of the most prevalent challenges for travel organizers is the efficient planning of trips in terms of both time and cost. Many small-scale travel agencies resort to managing multiple online tools at a cost, but our all-inclusive platform streamlines this process by offering professional-grade tools that facilitate the creation of trip landing pages, automated billing schedules, and seamless back-office operations."

Having secured an impressive $1.5 million in funding, the startup has emerged as one of the few Black-owned travel software enterprises to garner over $1 million in investment. Backers include notable entities like TechStars, Forum Ventures, and Atento Capital, a Tulsa-based venture capital firm focused on unlocking unsung potential in early-stage founders.

SquadTrip's co-founders have generated $7 million in travel sales and facilitated 6,000 bookings. The business partners, who originally bonded as best friends during college, embarked on their entrepreneurial journey by establishing an event ticketing platform tailored for Black entrepreneurs. In 2022, they launched SquadTrip.

Watson recollects, "The concept for SquadTrip emerged while helping a friend create a simpler way to collect money for his birthday trip. Our software system transformed his annual group excursion into a million-dollar travel enterprise."

The automated payment solution caters to professional group trip organizers, travel agents, and travel brands, but it also suits travel enthusiasts who regularly organize trips for family and friends. Be it a significant milestone celebration or a family reunion, users can access SquadTrip's platform free of charge, paying a mere 6 percent fee per booking.

Stevon Judd, CTO and co-founder of SquadTrip, reveals, "Initially, our focus was on our ideal customer base, but we soon realized that our platform resonates with a wide array of travel professionals and enthusiasts. Our users span travel agents, destination wedding planners, retreat organizers, and even leisure travelers who arrange trips for their loved ones."

Group travel often involves coordinating multiple aspects such as transportation, accommodations, activities, and itineraries for a larger number of people. This complexity can lead to logistical challenges, especially when dealing with last-minute changes, cancellations, or unforeseen circumstances. While small agencies might lack access to advanced travel management software and tools that larger agencies use to manage bookings and handle customer interactions, SquadTrip addresses these challenges by helping travel professionals work more efficiently and recover untapped revenue. 

Stephanie Kilson-Thomas, a SquadTrip customer and owner of KT Travel & More, explains, "The majority of my clients are destination wedding groups, and SquadTrip allows me to manage the reservations process for a large number of travelers from beginning to end."

With the recent investment funds, the company is strategizing to amplify its business presence, onboard fresh talent, and enhance its product offerings. A notable addition to the platform is a new affiliate feature that allows travelers to share trips with friends through a unique link. Users will be rewarded with cash when their referrals participate in the trip.

In the current year, SquadTrip has undertaken a full-scale relocation from New York to the Black-owned tech ecosystem in Tulsa's Greenwood District, renowned as Black Wall Street.

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Written by Nicole Blake-Baxter, PR and communications strategist driving dialogues within the ever-evolving worlds of tech and travel.

Pilot Is A Social Travel Hub That Uses AI To Help You Plan, Book And Share Trips

Pilot, a Vancouver-based startup, wants to connect people via travel and become "the hub of the global travel experience." To do that, the company has built an all-in-one social trip-planning platform

Founder and CEO of Pilot Connor Wilson, a serial entrepreneur, came up with the idea of Pilot in 2019 while traveling around Europe. Just after the start of the COVID-19 pandemic in 2020, when no one was traveling at all, he set up the outfit with a group of four founders. The beta of the app launched in 2022, and without any proactive marketing, Pilot quickly picked up 5,000 users. Now, that figure -- again, with no marketing to date -- has ballooned to more than 20,000.

Wilson believes the strong take-up has been because Pilot is filling a gap in the market.

"The traditional approach [of travel planning] is very siloed, rigid and surprisingly has no element of social connection that is a big part of traveling," he said in an interview. "So, we're starting from the travelers' perspective and embracing collaboration and personalization from the technical side."

But it is not building a social network, Wilson stresses. Pilot is more like "building consumer software with social functionality, closer to Google Docs, Notion and Strava than Facebook."

Yes, yes, we know: there are a lot of AI travel apps out there already. Wilson counters that Pilot is not an app that allows users to meet new people to travel together, nor is it an AI-powered travel agency.

"Users are not meeting new people via the Pilot app in a blind fashion. They control who they share their plans with," Willson said. "Our platform gives them tools to help them connect with and collaborate with their friends, family, and partners through travel."

Its AI trip planner, called Quickstart, generates an itinerary with personalized recommendations based on the user's traveling parties' preferences and allows users to request any edits or changes via chatting with the AI. Users can sign up, click "Create a trip," and select specific interests they want to include with a couple of clicks. The platform also helps users book stays and flights. After the travel, users can share their trips on its blog.

"It'll remind people of ChatGPT at first, but the visual layout and robust recommendations are what then make it feel unique," Wilson said.

Image Credits: Pilot

Pilot works on affiliate mode: it's free for consumers to use, and the company earns commissions from vendors when users book their travels through the Pilot platform. That being said, revenue has not been its focus now. "We've been building the platform to plan trips on and growing our community," said Wilson. "This has set us up to now explore the limitless opportunities for monetization."

Its web app is available to access worldwide, serving English-speaking countries; its mobile app is coming out later this year, he added. Pilot intends to expand further to the Latin American and Asia markets for travelers.

The outfit aims to benefit all types of travelers, but now its users are primarily underserved travelers. "Those that love to travel in groups of friends and backpackers, digital nomads, and remote workers looking to make the most of their shared experiences," Wilson says.

Pilot was also a part of the Creative Destruction Lab's accelerator program this year.

Pilot, which has raised roughly $650,000 from angel investors, is now looking to raise $4 million to focus more on building out its social side of the platform.

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Network Of Entrepreneurs Selling Travel Adds Business Analysts

The Network of Entrepreneurs Selling Travel (NEST) has expanded its team of business analysts, adding Serra Wheeler and Jen Duckworth to its ranks.

Serra Wheeler

The two analysts will also help recruit new agencies to join NEST, which hosts about 500 travel advisors.

The team is being expanded, NEST said, because of "skyrocketing" travel sales among member agencies.

Duckworth, most recently vice president of product development at Smart Travel Group, brings more than 25 years of experience in the industry to the role. At Smart Travel Group, she had also led the advisor-recruitment program, managed business-to-consumer operations, orchestrated conferences and oversaw the call center.

Jen Duckworth

Wheeler owned a travel agency affiliated with NEST for more than 15 years. Before that, her background was in computer science.

As business analysts at NEST, they will focus on helping members develop their businesses and provide personalized support.

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