Solo & Small Firm Side Gigs: Ivy B. Grey, Lawyer & Author of American Legal Style Guide for PerfectIt

In the past, I’ve groused about legal tech products that don’t work well  because they were designed without lawyer input.  That’s why today, I’m excited to introduce Ivy B. Grey, who is featured today as part of the MyShingle Profile Series, profiling  solo and small firm lawyers doing interesting things.  As Ivy discusses, she’s a practicing lawyer but she also plays a key role in adapting the PerfectIt proofreading and editing tool for lawyers and her influence is apparent. If you’re interested in legal tech but not ready to leave your day job, this profile may help you chart a path forward.

Let’s begin by discussing PerfectIt. When was it released and what does it do?

PerfectIt was originally released in 2009. It is a proofreading and editing add-in for MS Word that checks for errors using familiar spell-check-like functionality and informative commentary. It runs more than 20 tests that check for common errors. PerfectIt works with US and all international types of English, and can even be customized to fit house style. It delivers faster, more accurate proofreading and editing for professionals, ranging from copy editors and consultants to lawyers and scientists.

And what is American Legal Style?

“American Legal Style” is the legal-specific stylesheet that works inside of PerfectIt. It builds on PerfectIt’s basic checks and adds 13,000 corrections that only a trained legal writer or editor would know to look for. This style sheet transformed PerfectIt into a program that could reliably proofread and edit legal documents faster and more effectively.

American Legal Style pulls together guidance on legal writing so that lawyers can quickly apply the rules, style, guidelines, and writing techniques expected of them, without having to look up the information in several places. Using rules-based checks, it conforms your writing to the guidance found in The Redbook: A Manual On Legal Style by Bryan Garner, Typography for Lawyers by Matthew Butterick, the Elements of Style, and Black’s Law Dictionary, among others. It checks everything from consistent capitalization of defined terms and use of acronyms, to legal-specific typos and transposed letters in terms of art. It will also find formatting, spacing, spelling, and capitalization errors in Bluebook citations.

How does PerfectIt differ from built-in spell check on most word processors?

PerfectIt builds on spell check and grammar check. In the document creation workflow, PerfectIt comes after spell checking and before your final review and submission.

PerfectIt adds crucial capabilities missing in built-in tools. Spellcheck cannot:

  • Help with legal terms of art and can’t tell whether you’ve spelled them correctly.
  • Assist with Bluebook citations and can’t help you correct their spelling, spacing, capitalization, or punctuation.
  • Enforce consistency of capitalization or hyphenation across an entire-document.
  • Recognize incorrect idioms, particularly business idioms.
  • Recognize misused homonyms unless it is obvious.
  • Catch incorrect usage of properly-spelled words if they are uncommon or the usage is complex.
  • Enforce consistent use of numbers in sentences, punctuation, or heading style.

What are some of PerfectIt’s unique features?

Though there are several automated editing tools for legal writers, PerfectIt’s functionalities stand out for three reasons:

First, PerfectIt corrects the presentation and formatting of Bluebook citations. Thousands of corrections are focused on errors in citations such as misplaced periods, transposed letters in court and reporter names, incorrect capitalization, and missing or extra spaces. For example, now “E.D.T.X.” will be corrected to “E.D. Tex.” and incorrect citations to bankruptcy courts as “bank.” will be corrected to “bankr.”

Second, PerfectIt is unmatched in consistency-checking. Reviewing for consistency requires checking for capitalization of words, phrases, and headings; punctuation of bullet points and lists; hyphenation of prefixes, suffixes, terms of art, and defined terms; paired punctuation, such as quotation marks; and presentation of numbers. While there is other legal software that helps with enforcing some aspects of consistency in proofreading, none can match the depth, breadth, and accuracy of what PerfectIt does.

Third, PerfectIt improves performance but lets you write your way. It is the only legal writing program that brings together the most-respected leading legal writing guidance but still allows the author to write her own way.

Finally, PerfectIt is inexpensive. PerfectIt with American Legal Style costs just $70 per year.

What kind of response have you gotten from PerfectIt’s users?

PerfectIt is the leading software for professional editors worldwide. More than 6,000 users in 72 countries use PerfectIt. And around 300 law firms are using American Legal Style. People who try PerfectIt love it.

These reviews and more can be found on our website. PerfectIt also has more than 100 online reviews and a 4.5 star rating in the Microsoft Office Store.

  • “I may never again send out a document without first running PerfectIt. PerfectIt is like having a virtual, eagle-eyed proofreader on your staff.” Bob Ambrogi, LawSites
  • “We traffic in words. We are judged on our precision, accuracy, and clarity. PerfectIt is an automated copy editor armed with a thousand-point checklist. The formatting, grammar, spelling, punctuation, and consistency rules flag in matter of seconds what hours of human proofreading would likely miss.”
    Casey Flaherty, Principal, Procertas
  • “I’m a perfectionist, so I use American Legal Style for PerfectIt at the end of every letter and every other document that I create. I find it saves me an hour or more each time that I use it.”
    Heather Fathali, Immigration Attorney, Cascadia Cross-Border Law

What are the company’s future plans for PerfectIt?

In March 2019, we’ll be celebrating our 10-year anniversary. So, for our tenth year, we have an exciting and busy schedule of releases.

  • May 31: We launched the new website with content tailored for legal users. The tailored experience starts at
  • June 26: PerfectIt Cloud will be officially released. PerfectIt Cloud makes existing PerfectIt features available to Mac users for the first time. It will also work on iPads.
  • Aug/Sept: American Legal Style 3.2 will be released. There are currently 13,000 legal-specific corrections in American Legal Style. In version 3.2, this will be doubled.
  • Nov/Dec: PerfectIt 4 release. It includes new features for all users, including many more for lawyers, and there’s an automatic upgrade for everyone who purchased after May 31.

Turn our attention to your involvement with Perfect It? What is your connection to PerfectIt?

I am the creator of American Legal Style for PerfectIt, which is our flagship product for the legal field. With the introduction of American Legal Style, I adapted PerfectIt to work better in the legal context. Continuing to develop and improve American Legal Style is still the core of my work, including engaging with our users directly and through social media. Right now, I’m working on version 3.2 that will add thousands of corrections based upon my continued legal practice and feedback from our users.

I’m also the director for the legal sector, which means I’m responsible for developing all of our legal-specific content and strategy and working to collect and integrate feedback from our legal users.

How did you get involved with the company?

My route to legal tech was accidental and indirect. While I had worked in IT in college and was a bit of techie and an early adopter, I expected that my career would involve using legal tech—not creating it. That was until a friend asked me to try his proofreading add-in for MS Word. I did, and could see its potential if it were modified to be a better fit for lawyers. That friend was PerfectIt founder Daniel Heuman. We discussed my feedback and how I could see PerfectIt evolving. After that conversation Daniel asked me to join him and build the solution that I envisioned. The result is American Legal Style.

Now as I understand, you still work as an attorney at a law firm. Can you tell us about your practice?

I am a senior attorney at Griffin Hamersky LLP, which is a bankruptcy boutique in New York. One of our significant representations is In re Filmed Entertainment Inc. (Columbia House). My practice areas are business bankruptcy and commercial law. I work remotely from Chicago and am in my New York office about once per month. I practice law less than full time, and the ratio of legal practice to legal tech is constantly shifting by the week or month.

How do you balance your job at your firm with your role in PerfectIt?

I had worked with the two partners of the firm—Scott Griffin and Mike Hamersky—at another firm. We knew each other’s work well and fully trusted and believed in each other. This prior relationship with its foundation of trust and respect gives me the flexibility and autonomy necessary to have two demanding careers at once. To make it work, I have to structure my work into self-contained modular units where I can work intensely for stints, but don’t need to be involved daily.

Do you think that you will ever make PerfectIt a full-time job?

Right now, as we prepare for a big year of company updates and new software releases, PerfectIt has become a full-time job for me. But after this sprint, my role in product design will become more cyclical and less day-to-day. I have no plans to make PerfectIt my full-time job on a long-term basis. We’re a small company and we produce a low-cost product. So it doesn’t make sense to have a large, expensive team. We have a CEO and a full-time development team that are beautifully executing the plans to grow and update PerfectIt within a tight budget.

What advice do you have for other attorneys who are interested in working for a tech company or any company for that matter as a side gig?

If you want to be a creator, there are many paths to get there. You can learn to code; join forces with someone who shares your passion and has complementary coding skills; or you can offer yourself to adapt technology that you already love and bring it into the legal space. Examine your experience for how you can contribute and what unique skills or approaches you have. Keep those in mind when you offer to get involved or share your ideas.

Any other thoughts?

Thank you so much for inviting me to do this interview. I love MyShingle and I relied on it greatly when I was helping start my law firm. It’s an honor to be profiled here.

I’d also like lawyers to re-think how they approach tech tools for legal writing. Legal writing is a key part of what we do and it’s important that we’re deeply involved in creating the final written work. But our value comes from our arguments, structure, and creative solutions. It doesn’t come from the act of typing. Yet, sloppy typing and ineffective proofreading can diminish the value of your hard work and tarnish your reputation. PerfectIt can automate work that is low value and error-prone so you can focus on practicing at the top of your law license doing substantive, important work instead.

If you’re not sure about whether PerfectIt or any other legal writing tech tool is right for you, there is a 14-day free trial of the full version.