Account Exec, Tac Workflow Interview Prep

Tell me about yourself.

Sure. I’m currently a Specialist, Clients & Markets at Ryan, where I focus primarily on business development within the tax services space.

A big part of my role is identifying the right decision-makers within prospective accounts and reaching out through cold calls and email to generate new business opportunities. I work heavily in Salesforce, ZoomInfo, and LinkedIn Sales Navigator to manage my outreach and activity.

One of the biggest things I’ve developed at Ryan is the ability to take a completely cold account, get the right person engaged, work through objections, and ultimately get them in front of our tax experts.

I’ve enjoyed that side of sales, but I’m at the point where I want to take the next step and own more of the sales process.

That’s a big reason this Associate Sales Executive position stood out to me. It gives me the opportunity to build on the outbound sales and tax-industry experience I already have while developing into a full-cycle Sales Executive.

Why are you looking to leave Ryan?

The biggest reason is career progression. My current role is primarily focused on the front end of the sales process. So, identifying the appropriate contacts, engaging cold prospects, and generating meetings for our tax professionals, but I’m not the person who owns that opportunity through the rest of the sales cycle.

I’ve gotten to the point where I want that additional responsibility. I want to handle more of the sales process and ultimately be responsible for closing business and generating revenue.

So I’m not looking to leave Ryan because of something negative. I’m looking for an opportunity where I can take the experience I’ve built and move into the next stage of my sales career.

So you're looking for a closing role?

Yes. I want to continue prospecting because I think that’s an important skill for any salesperson, but I also want the opportunity to own what happens after I create that opportunity.

Why Thomson Reuters?

There are a few things. The first is Thomson Reuters is an established company where I’d have the opportunity to sell solutions into a market I already have experience working in.

I’m not trying to make a completely unrelated career change. I’ve spent years working in tax services at Ryan and Altus before that, so I’m familiar with selling into tax and finance departments.

And also I’d have the opportunity to make the transition into full-cycle sales and ideally build a long-term career rather than simply taking any another sales job.

Why this Associate Sales Executive position?

This position feels like a natural next step from what I’m already doing.

I have experience with the outbound side of sales — identifying decision-makers, prospecting, cold calling, working in Salesforce, handling objections, and creating opportunities.

What I’m looking for now is the opportunity to take those skills and expand them into the rest of the sales cycle. This position would give me experience with product demos, pipeline management, closing, and eventually expanding existing customer relationships.

Why sales?

What I like about sales is that there’s a direct relationship between what you put into the job and the results you produce. I like having measurable goals and knowing where I stand.

With outbound sales especially, you’re starting with somebody who wasn’t necessarily looking to speak with you, and you need to communicate value quickly so you can ultimately have a second conversation, which would be the meeting/demo.

As I’ve gotten more experience, I’ve realized I want to take an opportunity from that first conversation all the way through to a closed deal.

What are you looking for in your next role?

There are three main things.

I want to move into full-cycle selling and have more ownership over the revenue I generate.

I want a strong training and coaching environment. I know I have a good foundation in outbound business development, but there are parts of the sales cycle I still need to develop, particularly demos, negotiation, and closing.

Lastly, I’m looking for somewhere I can grow long term. I don’t want to simply move from one business-development position into another. I want my next move to put me on a path toward becoming a Sales Executive.

What do you know about the position?

My understanding is that the position supports a territory while developing into a full-cycle sales role.

There’s a significant outbound component, and I’d be qualifying opportunities, conducting product demos, managing pipeline in the CRM, and helping drive new business, expansion, and renewal revenue.

It sounds very cross-functional because I’d be working alongside other Sales Executives and SDRs

Tell me about your current role at Ryan.

I’m currently a Specialist of Clients & Markets at Ryan. My role is focused primarily on generating new business opportunities across our different tax practices.

Accounts generally come to me in a couple of ways. I’ll work with our Principals on specific service-line campaigns, or I’ll receive accounts from our lead-generation team. From there, I use tools like ZoomInfo and LinkedIn Sales Navigator to identify appropriate decision-makers and then conduct outbound outreach through cold calling and email.

My goal is to get the right person engaged and ultimately schedule a meeting between that prospect or existing client and the appropriate tax professional on our team.

I use Salesforce heavily to track my outreach, maintain account history, schedule follow-ups, and keep my activity organized.

Because we sell professional tax services, a lot of my outreach is to senior-level contacts across tax, finance, accounting, and real estate teams.

Walk me through your sales process.

My process starts with understanding the campaign and who we’re trying to reach. Once I’m given an account, I use ZoomInfo and LinkedIn Sales Navigator to identify the appropriate decision-makers. I generally take a top-down approach, starting with senior-level contacts and then working through the relevant tax, finance, accounting, or real estate functions depending on the service.

From there, I begin outbound outreach through calls and email. My goal isn’t to explain everything Ryan does on the first call. It’s to establish why I’m reaching out, create enough value or interest to continue the conversation, and ultimately secure a meeting with the appropriate tax expert.

Once I secure the meeting, I hand it off to one of our tax professionals so they can take the conversation from there.

Throughout the process, I document my activity, conversations, and follow-ups in Salesforce so I know where each account stands.

How do you approach cold calling?

I prefer to be direct. I don’t want the first 30 seconds to sound like I’m reading a long sales pitch, especially when I’m speaking with senior executives who generally want you to get to the point.

I’ll introduce myself, explain why I’m reaching out, and give them a specific reason a conversation with us could be valuable. For example, if we know there’s been a significant increase in their tax liability, I can use that to explain why it may be worth having a conversation about whether there’s an opportunity to reduce it.

And I understand that most cold calls aren’t going to become opportunities. That’s why I think consistency, volume, and improving your pitch through trial and error are important parts of cold calling.

How do you handle rejection?

I’m pretty comfortable with rejection at this point. It happens so often and in so many different ways that it becomes a daily occurrence.

I try not to evaluate myself based on one call. I focus more on whether I’m consistently executing my scripts and generating results over a monthly basis.

At the same time, if I’m consistently hearing the same objection and I’m not having success getting past it, I’ll look at my messaging and adjust my approach.

So for me, handling rejection is really about not taking it personally, learning from it if it’s an objection I’ve heard for the first time, and moving on to the next opportunity.

How do you handle objections?

I’ll try to understand what’s behind the objection instead of immediately trying to overcome it.

The most common objection I hear is that they already have a property tax advisor. Rather than telling them why their current advisor isn’t good enough, I’ll acknowledge that relationship and ask a question — such as when they last evaluated their advisor’s performance or whether they’d be open to understanding if there could be additional savings beyond what they’re currently receiving.

That allows me to position Ryan as another perspective and a potential source of additional value rather than attacking an existing relationship.

Tell me about a difficult objection you've overcome.

One of the most difficult and common objections I deal with is a prospect telling me they’re already satisfied with their current tax advisor and don’t see a reason to have another conversation.

When I get that response, I don’t try to convince them that they need to replace their advisor. I acknowledge that having an established relationship makes sense and change the positioning of the conversation.

I’ll explain that having a conversation with Ryan doesn’t necessarily mean replacing anybody. The value could simply be getting another perspective on their portfolio and determining whether there are additional opportunities their current approach may not be capturing.

That’s worked for me because I’m not asking them to immediately reconsider an established relationship. I’m asking them to consider whether a second review could provide additional value. I’ve been able to use that approach to turn that initial objection into meetings with our tax team.

How do you identify and research prospects?

It depends on the campaign because the right contact can change depending on the service we’re selling.

For property tax, for example, I’ll generally look for contacts across tax, finance, and accounting teams. For a 45L energy-efficient home credit campaign I worked on, the relevant contacts were more likely to be in development, construction, real estate, or asset management.

Once I understand who is likely to be involved in that particular decision, I use ZoomInfo and LinkedIn Sales Navigator to identify the appropriate people within the account.

Timing can also be important in tax. For certain campaigns, an upcoming appeal or filing deadline creates a natural reason for us to reach out and can make the conversation more urgent.

How do you identify the right decision-maker?

Because I’ve worked on so many campaigns, I generally have an idea of the contacts who would mot likely be the DM.

For property tax, that might be somebody in tax, finance, or accounting, depending on how the company is structured. For something like the 45L energy-efficient home credit campaign I worked on, I targeted contacts in areas like development, construction, real estate, and asset management.

I’ll use ZoomInfo to identify likely contacts, and then I can further confirm the right person through my calls and emails.

One thing I’ve learned is not to get overly attached to a specific job title because the person responsible can vary significantly depending on the company and its size.

How do you prioritize accounts?

In my current role, the accounts and campaigns I work are generally assigned to me, so I’m not independently deciding which companies enter my pipeline. The campaign itself will also usually tell me where there’s urgency, such as an upcoming tax deadline.

Within those assigned accounts, though, I still have to prioritize my day-to-day activity. An active follow-up with someone I’ve already spoken to takes priority over a completely cold contact, and an account with a time-sensitive deadline takes priority over one without that same urgency.

So I’d say my current role has taught me to prioritize primarily around urgency and engagement. In a territory-based role where I had more ownership over account selection, I’d consider factoring in things like account potential and likelihood of an opportunity.

How do you organize your day?

I start my day by looking at what I have scheduled — internal meetings, follow-ups, and any emails that need an immediate response.

From there, most of my time is dedicated to whatever campaign I’m working on and the stage I’m at. That could mean identifying contacts, performing outbound outreach, following up with people I’ve already contacted, or updating Salesforce with activity and notes.

I try to batch similar activities together when I can because constantly switching between research, calls, emails, and administrative work makes me less efficient.

At the end of the day, I’ve handled the important follow-ups while still performing enough outbound activity.

How do you manage a high volume of prospects?

The biggest thing for me is having a system so I don’t have to rely on memory.

I use Salesforce to document conversations, track my outreach, create follow-up tasks, and keep good notes on interactions.

I also treat contacts differently depending on where they are in my outreach. Someone I’ve already spoken with who asked me to call back next week obviously gets treated differently from somebody I’ve never contacted.

When you’re working a large number of accounts, being able to open an account weeks later and immediately understand what happened in the previous conversation makes a big difference, so good notes in SF are very important.

How do you use Salesforce?

I use Salesforce every day to manage my prospecting activity and account history.

I use it to review accounts, document calls, log outreach, maintain contact information, create follow-up tasks, and look at previous interactions Ryan may have had with an organization.

I’m very comfortable working in Salesforce because it’s a major part of how I manage my day-to-day.

Tell me about your experience selling to senior decision-makers.

A lot of my outreach at Ryan is directed toward senior-level contacts, so I’ve become very comfortable cold calling executives.

One thing I learned quickly is that you have to respect their time. You can’t spend two minutes explaining your company before giving them a reason to care. That’s part of why I prefer a direct approach — I want to tell them who I am, why I’m calling, and why it could be relevant to them as efficiently as possible.

It wasn’t easy when I first started, but after doing it consistently for years, I’m comfortable speaking with executives.

How do you build rapport with a prospect?

I don’t necessarily think rapport has to mean a lot of small talk, especially on a cold call.

Because I often work campaigns across a large number of accounts, I’m not doing extensive individual research on every person before every call. What I do know is the reason behind the campaign, the value Ryan can potentially provide, and why that service could be relevant to the type of company or contact I’m targeting.

I try to be personable without forcing a personal connection. I think credibility, listening, and being respectful of their time is what builds rapport.

How do you qualify an opportunity?

Formal opportunity qualification isn’t part of my responsibility.

The accounts I work are generally provided through our tax professionals or our lead-generation team. For example, I’ll meet with a Principal who explains the service line and the group of accounts they want me to target, or I’ll receive HELP accounts from our lead-generation team, which are accounts where other sales teams have had difficulty getting engagement.

My responsibility is primarily to identify the appropriate contacts, conduct the outreach, work through objections, and create the initial opportunity by securing the meeting.

And so, that’s actually one of the skills I’d like to develop in a full-cycle role.

You haven't been responsible for closing. Why should we believe you can?

That’s fair. I don’t have direct closing experience yet, and I wouldn’t pretend that I do.

What I do have is several years of experience creating opportunities where one didn’t exist before. I’m comfortable cold calling, dealing with rejection, navigating objections, identifying decision-makers, working in a high-volume environment, and consistently trying to turn cold accounts into actual conversations.

The next skills I need to develop are things like deeper discovery, product demonstrations, negotiation, and closing.

That’s why I’m looking at this opportunity, to build those skills with coaching while bringing a strong outbound foundation.

Are you comfortable continuing to prospect even though this is a closing role?

Absolutely. I’m not looking at full-cycle sales as a way to stop prospecting.

What I’m looking for is the opportunity to continue prospecting while also taking ownership of what happens after I create the opportunity.

You've been at Ryan for several years. Why haven't you moved up internally?

That’s something I’ve actually been discussing with my manager for about the last two years. I’ve been transparent that I want to continue developing and take on more responsibility beyond my current position.

We’ve had several conversations about what that progression could look like, and more recently there were discussions about creating a senior-level position. Because there seemed to be a path developing internally, I was willing to be patient and continue performing in my current role while that was being worked out.

But more recently, my manager decided to leave the company. Which has caused me to reevaluate where I am and rather than continuing to wait for an internal opportunity that may or may not materialize, I’ve decided it’s the right time to explore other opportunities.

Why have you stayed at Ryan for so long?

But if you've wanted to advance for two years, why didn't you leave sooner?

A.

I’ve stayed because I’ve had a good experience at Ryan and I’ve continued to develop professionally. I’ve gained a lot of experience in B2B prospecting, learned how to communicate with senior decision-makers, developed a much stronger understanding of the tax industry, and become very comfortable in a high-volume outbound environment.

For roughly the last two years, I’d been having conversations with my manager about taking the next step internally, and more recently there were discussions about a potential senior-level position. I felt it was worth giving that opportunity a chance to develop.

With my manager recently leaving the organization, the circumstances changed. It feels like the right time for me to look externally for an opportunity where I can take what I’ve learned and move into the next stage of my career.

B.

Because I believed there was still a realistic opportunity to advance internally.

I had a good relationship with my manager, we had discussed my career goals multiple times, and I had been told that a senior-level opportunity was being worked on. I thought it was worth being patient and giving that opportunity a chance rather than leaving prematurely.

Once the circumstances changed and my manager left, I reassessed where I was. At this point in my career, I’m ready for more responsibility, and I don’t want to continue waiting indefinitely for an opportunity that isn’t clearly defined.

Questions for Them

1. What does success look like in the first 90 days?

2. What does the training process look like, particularly for someone transitioning from business development into full-cycle selling?

3. What does the typical career progression look like from this position?”

4. What separates your top-performing Associate Sales Executives from those who struggle?

5. What does the typical sales cycle look like—from the initial conversation through close?

1. I saw the target total cash compensation range on LinkedIn. Could you walk me through how compensation is structured between salary and incentive?

2. Are there accelerators for exceeding quota?

3. What's a typical deal size?

4. How much of my pipeline is expected to be self-generated versus coming from SDRs, or existing customers?