Starting Career: BigLaw or Elite Boutique?

[Anonymous User]

(Anonymous because of the small class size, any additional information would out me)

What are the pros and cons to starting at a boutique? Basically, I'm unusually stressed right now and having a hard time, so I would appreciate anyone's thoughts or things they think I should consider. I have one offer in hand and expect the second when I finish my other program in the next couple of weeks.

If all goes according to plan, I'll be deciding between a V5-V15 BigLaw firm headquartered in my non-NYC, non-DC major market and one of the elite (in my opinion) tax/benefits boutiques (Caplin & Drysdale; Miller & Chevalier; Ivins, Phillips & Barker; Roberts & Holland; Groom Law Group). I'll do some general points and then firm-specific points.

General Background:

• I'm interested in tax and ERISA/Employee Benefits and will do that work at either firm.
  I value consistency/predictability (if possible).
  Neither firm has cut salaries, laid off staff, or cut my summer money (the BigLaw firm shortened it but still paid for 10 weeks).
  I will graduate with no debt (super fortunate).
  Both firms pay market though I expect some compression at the boutique after year three.
  Both firms are chambers-ranked

BigLaw Firm

• Hours Requirement: 2,000-hour for bonus

• Bonus: Market

• Clients: Large public companies and some private equity

• Tax Group: Primarily deal support with some controversy and some counseling. Large enough to have specialties (though it only matters when you're more senior): M&A, Bankruptcy/Reorgs, SALT, Tax-Exempt Orgs, Real Estate

• EB Group: Roughly a 50-50 mix between counseling and transaction due diligence

• Partnership prospects: Standard BigLaw

• General takeaway: Associates in both groups seem relatively happy. People seemed busy all the time and their schedules were largely unpredictable. Meetings got moved a lot and associates/partners were consistently late or had to drop off early. Assignments didn't seem to be super complex (I don't know if this is indicative of the group or just me being a summer). Access to a lot of support staff/resources.
  A lot of structure.

Boutique

• Hours: 1,800 requirement (actual hours seem to not be far off)

• Bonus: No bonus, maybe profit sharing

• Clients: Large public companies, high net-worth individuals, large privately-held corporations

• Tax Group: Controversy, counseling, and some legislative and administrative lobbying. People are more generalized in some ways but also have carved out some impressive niches. Have a well-known international tax practice, tax-exempt orgs, corporate

• EB Group: Counseling with some legislative and administrative lobbying

• Partnership prospects: Strong chance of partnership and shorter path (6 years or so). It is small so people are hired to become partners in the future.

• General Takeaway: Associates seem genuinely happy. People seem to be busy but not overwhelmingly so -- meetings generally didn't get delayed or moved. Assignments seem more complex (same caveat as above). Less support staff/resources. Less structure.

Just curious what people think about starting at a boutique vs. BigLaw firm. I appreciate tax-specific or general boutique advice.

I don't really know how exit opps work with the boutique. BigLaw has your standard exit opps. I think the boutique should probably let me go to BigLaw or in-house if I wanted to as it is a well-known name in tax, but I don't really know as people don't seem to leave that often. The boutique definitely provides some unique exit opps and is well-connected for IRS/Treasury positions and House/Senate tax policy positions, which would be cool. I know some people have left to these and then come back to the firm. I am worried that the boutique could be more limiting if I decide/need to leave in the future -- though I generally imagine myself working there long term.

In general, I think I am leaning towards the boutique but don't know if there are other things I haven't thought of.

I appreciate any advice, comments, corrections, or considerations. If the actual firm would change your answer, say which one and let me know why.

Thanks!

[Lacepiece23]

(Anonymous because of the small class size, any additional information would out me)

What are the pros and cons to starting at a boutique? Basically, I'm unusually stressed right now and having a hard time, so I would appreciate anyone's thoughts or things they think I should consider. I have one offer in hand and expect the second when I finish my other program in the next couple of weeks.

If all goes according to plan, I'll be deciding between a V5-V15 BigLaw firm headquartered in my non-NYC, non-DC major market and one of the elite (in my opinion) tax/benefits boutiques (Caplin & Drysdale; Miller & Chevalier; Ivins, Phillips & Barker; Roberts & Holland; Groom Law Group). I'll do some general points and then firm-specific points.

General Background:

• I'm interested in tax and ERISA/Employee Benefits and will do that work at either firm.
  I value consistency/predictability (if possible).
  Neither firm has cut salaries, laid off staff, or cut my summer money (the BigLaw firm shortened it but still paid for 10 weeks).
  I will graduate with no debt (super fortunate).
  Both firms pay market though I expect some compression at the boutique after year three.
  Both firms are chambers-ranked

BigLaw Firm

• Hours Requirement: 2,000-hour for bonus

• Bonus: Market

• Clients: Large public companies and some private equity

• Tax Group: Primarily deal support with some controversy and some counseling. Large enough to have specialties (though it only matters when you're more senior): M&A, Bankruptcy/Reorgs, SALT, Tax-Exempt Orgs, Real Estate

• EB Group: Roughly a 50-50 mix between counseling and transaction due diligence

• Partnership prospects: Standard BigLaw

• General takeaway: Associates in both groups seem relatively happy. People seemed busy all the time and their schedules were largely unpredictable. Meetings got moved a lot and associates/partners were consistently late or had to drop off early. Assignments didn't seem to be super complex (I don't know if this is indicative of the group or just me being a summer). Access to a lot of support staff/resources.
  A lot of structure.

Boutique

• Hours: 1,800 requirement (actual hours seem to not be far off)

• Bonus: No bonus, maybe profit sharing

• Clients: Large public companies, high net-worth individuals, large privately-held corporations

• Tax Group: Controversy, counseling, and some legislative and administrative lobbying. People are more generalized in some ways but also have carved out some impressive niches. Have a well-known international tax practice, tax-exempt orgs, corporate

• EB Group: Counseling with some legislative and administrative lobbying

• Partnership prospects: Strong chance of partnership and shorter path (6 years or so). It is small so people are hired to become partners in the future.

• General Takeaway: Associates seem genuinely happy. People seem to be busy but not overwhelmingly so -- meetings generally didn't get delayed or moved. Assignments seem more complex (same caveat as above). Less support staff/resources. Less structure.

Just curious what people think about starting at a boutique vs. BigLaw firm. I appreciate tax-specific or general boutique advice.

I don't really know how exit opps work with the boutique. BigLaw has your standard exit opps. I think the boutique should probably let me go to BigLaw or in-house if I wanted to as it is a well-known name in tax, but I don't really know as people don't seem to leave that often. The boutique definitely provides some unique exit opps and is well-connected for IRS/Treasury positions and House/Senate tax policy positions, which would be cool. I know some people have left to these and then come back to the firm. I am worried that the boutique could be more limiting if I decide/need to leave in the future -- though I generally imagine myself working there long term.

In general, I think I am leaning towards the boutique but don't know if there are other things I haven't thought of.

I appreciate any advice, comments, corrections, or considerations. If the actual firm would change your answer, say which one and let me know why.

Thanks!

I'd take the money unless I was absolutely sure that I'd work 200 hours less at the boutique. I'd still probably take the money.

[nealric]

There are good arguments either way. However, I'd lean boutique since you seem to be more on the benefits side.

The reason to go biglaw is that you will get exposed to larger deal work, which the firm itself will be hired for rather than being hired as a tax-specific consultant. If you are more on the benefits side, the deal work likely won't be as key to development (compared to someone who wants to do M&A tax, for example). My impression is the boutiques are more controversy heavy, so that may factor in.

All that said, the personalities involved will be key. The #1 most important thing for a new lawyer is to get good mentorship and development. You need to be working under partners who take an interest in you. The boutique is more likely to take an interest in your development and less likely to push you out as you get more senior, but could be a nightmare if you have a personality clash because there's nowhere to "escape to". That said, most biglaw firms have very small tax/benefits groups, so it can feel like working for a boutique within a larger organization.

[Anonymous User]

I’ve worked in both settings, and I agree with the above that it depends on what you’re looking to do. However, I’m 90% sure I know which boutique you’re considering and I don’t know if you can do just employee benefits there.

You mentioned that the biglaw firm is 50% counseling, which is great. But the type of counseling you do at a big, transactional firm is almost always limited to 409A, 4960, or 457(f), or investment funds (Title I) for fund clients. Clients are not as willing to pay that much for ERISA or QP advice, especially from what I’d call a benefits generalist.

Deal due diligence gets boring really quick. The work becomes formulaic after the first year. The checklists, the reps and warranties, the waivers and consents, etc.

But on the other end, some ERISA work is mind-numbingly boring and almost secretarial, even at the boutiques.

One thing to consider is that unlike some practices, transitioning from a general counseling/controversy role at one of the boutiques to a role at a deal firm (or vice versa) is actually difficult. The work doesn’t really overlap at the associate level. Partners at both seem to know all of it (mostly because many of the very senior ones were around for the beginning of ERISA, the senior ones had to deal with the PPA in 06, and many of the junior ones had to deal with ACA, which also involves ERISA).

Personally, if I had to do it again, I would start at a biglaw firm. Boutique life in general was difficult. There’s less support and the low leverage makes things extremely stressful. I don’t know if I could’ve handled that kind of stress as a first year on top of trying to learn ERISA.

[sms18]

Agree with the above posters and nothing much to add to what was already said. Just a couple of things to note are that, if you don't know for certain what it is that you want to practice (e.g., tax and ERISA/benefits are not at all the same and the exposure you get as summer isn't too helpful, especially in a remote work setting), biglaw is a better option since you're trained more of a "generalist" and some firms may allow you to try both tax and ERISA/benefits as a junior. In terms of exits, I've seen biglaw attorneys transition to tax/ERISA boutiques but haven't really seen the other way around. So with biglaw you may be able to keep your options relatively more open compared to the boutique (which may be preferable given the current economic climate and general uncertainty).

[Anonymous User]

Agree with the above posters and nothing much to add to what was already said. Just a couple of things to note are that, if you don't know for certain what it is that you want to practice (e.g., tax and ERISA/benefits are not at all the same and the exposure you get as summer isn't too helpful, especially in a remote work setting), biglaw is a better option since you're trained more of a "generalist" and some firms may allow you to try both tax and ERISA/benefits as a junior. In terms of exits, I've seen biglaw attorneys transition to tax/ERISA boutiques but haven't really seen the other way around. So with biglaw you may be able to keep your options relatively more open compared to the boutique (which may be preferable given the current economic climate and general uncertainty).

The anon poster who worked in both settings. I agree with this generally, except for the benefits/comp lateral from biglaw to boutique. I’ve seen many people make that transition for tax very regularly. For benefits, I don’t think it’s very common, but this may have to do with the fact that there are maybe like 10 ERISA associates at all of the boutiques combined.

A friend of mine applied to a mid-level opening for a benefits position at one of the boutiques with honors at a T6 and law review and a V10 and didn’t get an interview because the firm wasn’t looking for a transactional attorney.

The exception to the above are probably Morgan Lewis, Covington, and Proskauer since all have very robust ERISA teams.

[Anonymous User]

I’ve worked in both settings, and I agree with the above that it depends on what you’re looking to do. However, I’m 90% sure I know which boutique you’re considering and I don’t know if you can do just employee benefits there.

You mentioned that the biglaw firm is 50% counseling, which is great. But the type of counseling you do at a big, transactional firm is almost always limited to 409A, 4960, or 457(f), or investment funds (Title I) for fund clients. Clients are not as willing to pay that much for ERISA or QP advice, especially from what I’d call a benefits generalist.

Deal due diligence gets boring really quick. The work becomes formulaic after the first year. The checklists, the reps and warranties, the waivers and consents, etc.

But on the other end, some ERISA work is mind-numbingly boring and almost secretarial, even at the boutiques.

One thing to consider is that unlike some practices, transitioning from a general counseling/controversy role at one of the boutiques to a role at a deal firm (or vice versa) is actually difficult. The work doesn’t really overlap at the associate level. Partners at both seem to know all of it (mostly because many of the very senior ones were around for the beginning of ERISA, the senior ones had to deal with the PPA in 06, and many of the junior ones had to deal with ACA, which also involves ERISA).

Personally, if I had to do it again, I would start at a biglaw firm. Boutique life in general was difficult. There’s less support and the low leverage makes things extremely stressful. I don’t know if I could’ve handled that kind of stress as a first year on top of trying to learn ERISA.

OP here. Would you mind comparing and contrasting your experiences and what it was that you didn't like about working at one of the boutiques? How did you make the jump from boutique to BigLaw?

[Anonymous User]

OP here. So the general consensus seems to be that BigLaw is probably better for non-controversy tax. A boutique might be a better match for controversy and ERISA/EB.

I'll divulge a little more about myself so any advice can be more tailored: When it comes down to it, I really enjoy doing legal research, particularly tax research. I like reading and finding answers to things. I don't care much for marking up contracts or negotiating reps and warranties (at least as far as I can tell). I wouldn't mind marking up a contract/form if I felt like it was answering a question (i.e. we have new regulations and need to amend our form). But turning documents, at least as advertised in the corporate group, doesn't sound fun to me. Obviously, I'll take the bad with the good of a job but I'm curious how much of the corporate tax side of things involves marking up transaction documents vs. doing research?

I apologize for any dumb questions. Basing (what feels like) major life decisions off of working from home on a computer for four-six weeks without seeing actual work done is pretty difficult.

[Anonymous User]

I’ve worked in both settings, and I agree with the above that it depends on what you’re looking to do. However, I’m 90% sure I know which boutique you’re considering and I don’t know if you can do just employee benefits there.

You mentioned that the biglaw firm is 50% counseling, which is great. But the type of counseling you do at a big, transactional firm is almost always limited to 409A, 4960, or 457(f), or investment funds (Title I) for fund clients. Clients are not as willing to pay that much for ERISA or QP advice, especially from what I’d call a benefits generalist.

Deal due diligence gets boring really quick. The work becomes formulaic after the first year. The checklists, the reps and warranties, the waivers and consents, etc.

But on the other end, some ERISA work is mind-numbingly boring and almost secretarial, even at the boutiques.

One thing to consider is that unlike some practices, transitioning from a general counseling/controversy role at one of the boutiques to a role at a deal firm (or vice versa) is actually difficult. The work doesn’t really overlap at the associate level. Partners at both seem to know all of it (mostly because many of the very senior ones were around for the beginning of ERISA, the senior ones had to deal with the PPA in 06, and many of the junior ones had to deal with ACA, which also involves ERISA).

Personally, if I had to do it again, I would start at a biglaw firm. Boutique life in general was difficult. There’s less support and the low leverage makes things extremely stressful. I don’t know if I could’ve handled that kind of stress as a first year on top of trying to learn ERISA.

OP here. Would you mind comparing and contrasting your experiences and what it was that you didn't like about working at one of the boutiques? How did you make the jump from boutique to BigLaw?

The best part of a boutique is the hours. The hours at the boutique are generally much better. Most of the boutiques have 1700-1800 hour requirements, and 2000 is considered a lot of hours.

I enjoy transactional work and drafting contracts (which you seem to like less), so that was the main reason biglaw > boutique for me. At a boutique, you deal with a lot of random esoteric questions regarding minute details that are really not that important to deal lawyers.

You need to be conversant on a topic a day after the IRS/DOL release guidance and hopefully an expert shortly thereafter. When I was interviewing in the fall, the IRS had issued final regulations for hardship distributions. A few weeks later, I knew them inside out. My interviewer at a biglaw firm said, “oh. I had no idea those even came out. I’ll have to read them.”

Having to constantly keep up on small changes is tiring and not something I particularly enjoy. I like drafting contracts, doing change in control analyses, and other transactional work.

When lateraling, if you choose to go to a boutique first, you need to play up your 280G/409A experience. Depending on the firm you’re going to, you may not see that.

[Anonymous User]

Not OP, thank you for answering those questions. Do you think it's possible to do both transactional and tax controversy work in big law? I wonder what are the exit options for tax controversy attorneys. Thanks.

[Anonymous User]

Not OP, thank you for answering those questions. Do you think it's possible to do both transactional and tax controversy work in big law? I wonder what are the exit options for tax controversy attorneys. Thanks.

Relatedly, is it possible for someone with transactional tax experience to transition into controversy work?

[papermateflair]

OP here. So the general consensus seems to be that BigLaw is probably better for non-controversy tax. A boutique might be a better match for controversy and ERISA/EB.

I'll divulge a little more about myself so any advice can be more tailored: When it comes down to it, I really enjoy doing legal research, particularly tax research. I like reading and finding answers to things. I don't care much for marking up contracts or negotiating reps and warranties (at least as far as I can tell). I wouldn't mind marking up a contract/form if I felt like it was answering a question (i.e. we have new regulations and need to amend our form). But turning documents, at least as advertised in the corporate group, doesn't sound fun to me. Obviously, I'll take the bad with the good of a job but I'm curious how much of the corporate tax side of things involves marking up transaction documents vs. doing research?

I apologize for any dumb questions. Basing (what feels like) major life decisions off of working from home on a computer for four-six weeks without seeing actual work done is pretty difficult.

If you don't want to spend time marking up and turning purchase agreements, or doing due diligence, then I would not go into ERISA/EB at a big firm that is hiring you primarily to work on transactions. Not all big law ERISA/EB/EBEC groups work on transactions (and some folks do more counseling than others), but if your sense is that the group does more transactions, it doesn't sound like that's what you want to do, and it probably makes sense to go to the boutique and do more of the research/counseling work. Ask the associates you're connected with what their day to day looks like if you aren't sure how much actual planning/counseling they do vs transactional work.

Our controversy folks seem to be pretty siloed, and I don't think they do any transactional work. But it probably depends on how the group is structured and how badly they need associates to pitch in on things.

[Anonymous User]

OP here. So the general consensus seems to be that BigLaw is probably better for non-controversy tax. A boutique might be a better match for controversy and ERISA/EB.

I'll divulge a little more about myself so any advice can be more tailored: When it comes down to it, I really enjoy doing legal research, particularly tax research. I like reading and finding answers to things. I don't care much for marking up contracts or negotiating reps and warranties (at least as far as I can tell). I wouldn't mind marking up a contract/form if I felt like it was answering a question (i.e. we have new regulations and need to amend our form). But turning documents, at least as advertised in the corporate group, doesn't sound fun to me. Obviously, I'll take the bad with the good of a job but I'm curious how much of the corporate tax side of things involves marking up transaction documents vs. doing research?

I apologize for any dumb questions. Basing (what feels like) major life decisions off of working from home on a computer for four-six weeks without seeing actual work done is pretty difficult.

If you don't want to spend time marking up and turning purchase agreements, or doing due diligence, then I would not go into ERISA/EB at a big firm that is hiring you primarily to work on transactions. Not all big law ERISA/EB/EBEC groups work on transactions (and some folks do more counseling than others), but if your sense is that the group does more transactions, it doesn't sound like that's what you want to do, and it probably makes sense to go to the boutique and do more of the research/counseling work. Ask the associates you're connected with what their day to day looks like if you aren't sure how much actual planning/counseling they do vs transactional work.

Our controversy folks seem to be pretty siloed, and I don't think they do any transactional work. But it probably depends on how the group is structured and how badly they need associates to pitch in on things.

Anon who worked in both types of firms. While the above is true, a V5-15 aside from Covington will be transaction-related benefits and comp. Some do have Title I practice groups (Latham, for example), but most of the firms in the V5-15 range will be heavily deal-oriented.

Firms lower on the V100 (MLB, Dechert, and Venable, for example) or AmLaw firms that aren’t on Vault will probably do more broad benefits work. So if OP wants large firm, it may be worth finding one of these types of firms.