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An engineer seeks advice on landing a remote gig



Editor’s Note: Each week Maynard Webb, former CEO of LiveOps and the former COO of eBay, will offer candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at

Q. I’m an experienced engineering leader but I live in an area that doesn’t have a lot of high-tech companies, so I’ve been forced to work for companies that have jobs here. Given COVID-19 and the acceptance of remote work, I’m inspired to work for great tech companies that might not be in my geography. I’ve been in touch with several that had open positions, but I’ve been uninspired by the silence that I’ve received. Sometimes my résumé wasn’t even acknowledged, and if I did have a conversation the follow up was spotty at best. I have not received any explanation about why I didn’t get the job or any advice on what I can improve. What am I doing wrong and how can I get better?

 –Engineer trying to make a move

 Dear Engineer,

I commend you on your job search and trying to find better opportunities for work as well as trying to improve yourself. I’m sorry that you are facing this kind of treatment. I think it’s ridiculous for companies to treat people this way. Talent is the most important asset any company has—it should invest more in improving the recruiting process.

I wouldn’t leap to any conclusions (there’s not enough information to draw from) except to realize how many people are interested in these jobs. Don’t let any of this shake your confidence or resolve. In other words, keep trying and don’t take the radio silence personally.

As an experienced technology leader, you are one of luckiest people on the planet when it comes to searching for a job. I believe this will end well—with placement in a great company—but we first must figure out all the puzzle pieces.  

Is it possible there is something wrong with your résumé? Run spell check and make sure there are no errors. Read it carefully to see if any words were misused. These are things that spell check may not find. I can’t tell you how many résumés we see that have “there” instead of “their” or “hear” instead of “here.” These small errors can cost you a job.

 With résumés, less is more as hiring managers are scanning for key words. Make sure your key words are in there. Take out anything superfluous. Résumés are supposed to inform the reader about who you are and show your secret sauce, but this must be done succinctly and crispy. Think of a résumé as a way to inspire someone to want to have a discussion—it’s not a vehicle to share your life story. You want them leaning in when they read your résumé. After all, these people may be reading hundreds of résumés and they have no option other than to quickly determine if the candidate is worthy of an interview.

Connections always help. Can you have someone make introductions for you? Résumés sent cold may not make it to the top of the pile. You have a much better chance if someone recommends you. Many companies have employee referral programs; this is a good way to get noticed. A recommendation from an employee, board member, or other respected party will be helpful.

Have you tried to follow up? It is worth doing so as feedback is invaluable. Ask them why they passed and what you can do to improve. That said, use your judgement, you don’t want to be a pest in your reach out. At Webb Investment Network, we try to tell everyone we don’t hire or fund why we didn’t think it was a fit and we ask them to check in with us from time to time and keep us posted on where they end up and what they do. Staying in touch like this works; we can make mistakes in passing and perhaps we can all get a second chance.

I sincerely believe that companies can do better in how they treat people. Candidates who don’t have good experiences with companies will tell others who could decide not to apply. Companies would be well served to treat everyone with dignity and respect.

Keep knocking on doors and eventually one will open.

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Maura Healey approves gig economy ballot question but fights idea in court





“We better be able to walk and chew gum at the same time.”

Jessica Hill
Attorney General Maura Healey remains in a dichotomy after approving a ballot that would make gig economy workers independent, but continues to fight against Uber and Lyft in court to make drivers employees. Jessica Hill / AP

On Sept. 1, Attorney General Maura Healey gave the go-ahead to a ballot question that, if approved by voters, would maintain gig workers, such as Uber and Lyft drivers, as independent contractors.

At the same time, Healey and her office continue to spearhead a lawsuit against Uber and Lyft that accuses the rideshare companies of denying benefits to workers — whom she believes should be classified as employees, not contractors, under Massachusetts law.

On GBH’s Boston Public Radio segment “Meet the AG” Tuesday afternoon, host Jim Braude asked Healey to clarify the two simultaneous actions.

“We better be able to walk and chew gum at the same time,” Healey said. “Under the state constitution, there’s a process that allows regular folks to go ahead and get things on a ballot for a vote, and that happens every year … There may be litigation, there may not be litigation, but that’s just the hat that I wear as attorney general.”

Healey noted that her job is to review the ballot question’s language and to see whether or not it satisfies the legal requirements to make the ballot, regardless of her personal preference.

The ballot question garnered much attention in recent months as supporters — including a coalition of app-based businesses like Uber, Lyft, DoorDash and Instacart — argued that by keeping workers as independent contractors, the workers would be able to have more freedom with their job and set a minimum earnings guarantee. 

Opponents of the ballot question — like Healey — have said that it would continue to allow gig economy employers to provide less security for those who work for these companies. Throughout the pandemic, these companies have seen pushback from both gig economy workers and users on the treatment of employees. 

“As the economy grows, and work and the type of jobs change, there’s something they have to abide by,” Healey said. “We need to continue to treat workers fairly in this country, we need to make sure they’re not exploited.” 

Healey’s lawsuit, which was first announced in July 2020, asserts that rideshare drivers and similar workers should qualify as employees rather than independent contractors under Massachusetts Wage and Hour Laws.

In the lawsuit, Healey said her fair labor team determined that, under state law, gig workers should have access to minimum wage, earned sick time and other benefits and labor rights an employee would have. In March, the Suffolk Superior Court denied Uber and Lyft’s motion to dismiss Healey’s lawsuit. 

“Yes, gig workers and the gig economy are super convenient for all of us as consumers, right. There’s a price for that. And as we move forward with this gig economy, certain principles have got to abide. That’s why we have employment laws here in Massachusetts, and that’s why I’m in court against Uber and Lyft,” she said.

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This futuristic gig platform is owned by workers who keep 100% of earnings – The Hustle




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Five basic but essential steps to help take your side gig to the next level




The pandemic isn’t crushing the entrepreneurial spirit. It’s fuelling it.

People normally tied to a desk or working double shifts used lockdown to launch side hustles, often out of necessity. And some have turned those side gigs into full-fledged businesses.

According to the U.S. Census Bureau, 427,842 new business applications were filed in August 2021 alone. That figure was 288, 026 in August 2019.

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While a side gig can be spontaneous, growing a legit business requires research, planning and organization. Otherwise, your fledgling enterprise could crash and burn in a couple of years.

These basic but essential steps can help you take things to the next level and give your new venture a shot at staying power.


There are six common types of business entities: sole proprietorship, general partnership, limited partnership, C corporation, S corporation and limited liability company. The option you choose determines how your business is taxed, as well as who is financially responsible if your business is sued.

Entrepreneurs often default to sole proprietorship because it’s the easiest, but it’s also the riskiest, says Nellie Akalp, CEO and co-founder of, a document filing service that helps streamline the business formation process for entrepreneurs.

“There is no registration required nor are there corporate requirements,” Akalp says. But “there is no legal separation from the company, so the sole proprietor is personally responsible for any debts or liabilities.”

Registering as an LLC or corporation is more expensive and requires more paperwork, but it shields your personal assets from lawsuits.


Mixing business and personal finances can get messy, especially when it comes to filing taxes or securing a business loan. Open a business checking account to keep business income and expenses organized and easily accessible.

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Look for a business account that has low or no monthly fees and fits your business needs in terms of transaction and deposit limits.

A business credit card can also help you track expenses and identify tax deductions. Plus, you can earn rewards, like cash back on gas, office supplies and business consulting services.


No more manual spreadsheets or shoeboxes full of receipts; scale up to an accounting software that can do some of the heavy lifting for you, like tracking cash flow, managing invoices and generating reports.

Expect a learning curve with any new system, but know that it will help your operation run more smoothly. The right accounting software can also give you deeper insights into your business and help you identify weak points and opportunities to save money.

“Accounting is the language of business, so invest time and money into understanding how to do your books,” says Danetha Doe, founder of Money and Mimosas, a financial education platform for independent contractors, freelancers and small-business owners. “As a business owner, learning how to manage your company’s finances, read profit and loss statements, and understanding cash flows will make you a better entrepreneur.”


Your side hustle may have started organically, but turning it into a full-fledged business requires research and planning.

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Sketch out short – and long-term goals for your business, along with a sales plan, financial projections and potential roadblocks. Be realistic, set specific targets and spell out how you plan to reach them.

Building a business plan gives you a road map for how to grow your business. It also shows lenders you’ve done your homework should you need to secure a business loan.

Need help with your business plan? Turn to your local Small Business Development Center. These outposts are run by the U.S. Small Business Administration and offer free business consulting services.


Entrepreneurs, by nature, wear many hats. But you don’t need to wear all the hats.

Outsourcing some aspects of your business frees you up to focus on other things, like customer service or product development.

Not hip to social media? Consider hiring someone to build and manage your business’s presence on Instagram, TikTok and the like.

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Do tax forms make your eyes cross? Invest in a certified public accountant to file for you.

“CPAs may be more expensive than doing taxes on your own, but it will be done right,” says John Pham, founder of The Money Ninja, a personal finance website. “Plus, they will maximize your tax deductions, which will most likely give you a higher return than the cost of a CPA.”

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