“What are you looking to get out of this job?”
When does that ever go ever well in a job interview?
The same goes for negotiating a raise. “I want more money” is never a good response to “Why should we give you a raise?”
Asking for a raise should be based on your contributions to the sales org — revenue, efficiency, management. But framing all that the right way can be difficult.
We took this foundational question (“How do you ask for a raise?”) to the Sales Hacker community.
Every month, we’re asking the Sales Hacker community to share their perspective on sales (and sales-adjacent) topics with our entire audience. Want to participate? Respond to our survey, and you could be included in the next roundup!
What We Asked the Sales Hacker Community
This post reflects the responses of 26 Sales Hacker community members. Consider this more of a roundup of sales pros’ perspectives instead of deep research into navigating a raise.
Have you successfully negotiated a raise? This was a prerequisite for being included in the post. Instead of conjecture, we wanted real-world advice.
If yes, what did the process look like? Everyone’s career path looks different — this gave us a chance to dig into a more personal element of this conversation.
When do you think it’s a good time to ask for a raise? We left this one open-ended to get a sense of what matters — performance reviews, fiscal years, company performance, personal wins, and so on.
What is one valid reason you should ask for a raise? Same thing here. Instead of fishing for a narrative, we wanted to leave it open to see if a common theme emerged (and boy, did it).
What’s one winning tip for approaching the conversation? C’mon. This is sales. You didn’t think we’d leave you without the ‘quick tips’ and ‘silver bullets’ we all love, did you? (For skimmers: this’ll be closer to the bottom.)
Be Clear About the Why
Look, if you’re a high performer, your company will (in all likelihood) want to reflect that in your pay.
You just have to connect the dots. According to Mikey Harrison, Sales Hacker’s Partnerships Manager:
“If you consistently hit your number and are a valuable asset to the organization, it is in the orgs best interest to keep reps happy rather than have to ramp new employees,”
Arthur Castillo, an Account Executive, puts it a bit more bluntly:
“No one cares why you should get a raise; it’s all about how you’ve helped the company reach their goals.”
According to Arthur, the only reason to ask for a raise is to be rewarded for the value that you’ve brought to the company.
But no revenue-generating organization is going to give you a raise out of the goodness of their heart. You have to connect your ask to your contributions, your performance, and the company’s pipeline growth.
Nearly every single response held the same sentiment — tie your why to ROI.
Why should you ask for a raise?
These were some of the standout phrases from the Sales Hacker community:
- Exceeding expectations
- Mastering a role
- Overall performance
- Track record of quality work and accomplishments
- Blowing past your targets
- Taken on additional responsibility
It’s all about your contributions to the company.
But, let’s be real. This is still about you (at least for you, it is). More money in your pocket: more money to invest, donate to a charity, or buy avocado toast and Fortnite skins (I had to Google that last one).
You don’t have to be shy about communicating what you want.
The key is to bring both elements together.
Try this statement on for size:
“I believe I deserve an X% raise on my base salary because I’ve hit my quota x out of the last x months, and added $x to the pipeline. I’ve been a valuable team member and will continue to give my best with the recognition for my efforts.”
Keith Campagna, Chief Sales Officer at The ROI Shop, had one of my favorite responses.
Why should you ask for a raise?
“Because no one will ask for you.”
How Should You Ask For a Raise?
Ask 50 sales pros, and you won’t get 50 different answers — just 50 different versions of a similar perspective.
Let’s pull on the common threads for these tips.
#1: Get your timing right
The consensus from the Sales Hacker community? Timing isn’t everything… but it is really, really important.
When we asked, “When do you feel is a good time to ask for a raise?” very few community members included actual timelines — months, quarters, or years.
Instead, nearly every response had everything to do with where you are with the job — the accomplishments you’ve recorded, the resources you’ve added, and the successes you’ve seen within your responsibilities.
We saw this same sentiment put a few different ways.
Once you’ve proven yourself
You should wait until you have a track record of success. Here’s what a few people had to say on that front:
“Once you’ve shown your value to the org.”
Eva Poppe (Global Head of Sales Development)
“After showing your organization how important you are to their success.”
Lori Hopper (Account Executive)
“The right time comes when your contribution to the organization creates additional opportunities for revenue and exceeds position parameters.”
Julia Andrews (National Account Executive)
“When taking on more responsibility… or after a record of success is established.”
Tim Davis (VP of Worldwide Sales Engineering)
When the company is in the right spot
A handful of Sales Hacker community members added an important detail — be sure to tie your timing to the company as well.
You can ask for a raise when both “personal and company performance are up,” said Amanda Bagley, Account Executive at Chili Piper. Macky Bradley, one of Sales Hacker’s Channel Directors, agrees, saying that it makes sense to only make the ask “after a great quarter exceeding sales quota.”
At the right point in the year
Some responses focused on the calendar year (and some combined the two). “You can ask for a raise after exceeding expectations and having been at the company for at least a year,” said Adam Holt, an AE at a cloud finance company.
Kelly Venable, President at Your Hiring Coaches, provided exceedingly practical advice:
“Most of the time budgets are being solidified in October for the upcoming year… If you have been in your role for at least 9 months, a good time to start dialogue would be in September.”
Kelly also pointed out that you should ask for the meeting well ahead of formal reviews so that your ask will be taken into consideration.
(Note: adjust that date if your company operates on a different fiscal year.)
A handful of Sales Hacker community members (including two leaders, Lisa Bauer and Gia DeRose) recommend waiting until your formal performance review period.
Whatever your timing, the consensus is clear — tie your ask to your personal accomplishments, the company performance, and the value that you bring to the team.
#2: Be prepared — both with numbers and mindset
We’ve already seen one clear theme emerge from the Sales Hacker community responses — base your ask on your contributions.
There was only one theme that emerged even stronger — come prepared to the conversation with the data to back up everything you say.
Half the responses we received included some mention of data, numbers, and quantifying results.
Here are a few responses from those who reflected on their own conversations surrounding a raise:
“I made sure I had all my sales data from year one to show growth and progress. Let the data do the talking.”
– Chirag Jay Patel (Director of Partnerships)
“I collected stats to document why I deserved a raise. I also made sure that I was taking on additional responsibilities that were outside of my current role and documented success.”
– Kelly Venable (President @ Your Growth Coaches)
“It was a normal monthly OKR meeting. I pulled data from the previous 2 quarters prepared and started from there.”
– Amanda Bagley (Account Executive)
Beyond your own numbers, Arthur Castillo made a great point: have a good understanding of compensation in your industry. “Have salary insights into similar positions… Have a baseline for what you are looking for.”
Numbers are one thing — but what about your mindset?
“Prepare an agenda beforehand,” recommended Rishi Nair, a Global Partnerships Lead. “Preempt all possible outcomes and be prepared to counter each one of them.”
In other words: don’t just expect a simple yes or no.
Your boss could ask if you’d be willing to take on other responsibilities. They could say “Not right now, but what improvements are you planning to make?” They could counter your numbers with their own.
You should be ready for both a “no” and a bigger conversation or negotiation.
“Have a plan B,” Abhijeet Vijayvergiya said. “Do your prep just like one would approach a sales negotiation: with gives and gets.”
There were more than a few Sales Hacker community members who recommended treating the conversation when asking for a raise like a sales negotiation.
Your boss is your ICP (you’re already working for the company, after all), and you have to convince them that the ROI is worth the expansion.
#3: Remember the people part of the conversation
So far, we’ve focused almost exclusively on the utilitarian approach to asking for a raise: numbers, outcomes, self-interest and negotiation.
But there’s another critical element to asking for a raise: you’re still talking to people.
According to the Sales Hacker community responses, you’re probably best off treating asking for a raise like a sales conversation:
Be direct. Prospects don’t appreciate beating around the bush, and your boss won’t either.
Be confident. You come to your disco calls ready to go — this time, you’re selling yourself. “Keep your tone reasonable yet assertive and respectful,” as Director of Sales Jake Bernstein put it.
Be humble. Yes, you can be confident and humble at the same time. Try asking your boss for help instead of being combative to start.
Want to know what this looks like in practice? Check out this direct, confident, and humble example from JJ Steadman, Co-founder at Bobelo:
“The best raise I’ve ever negotiated led with me saying: ‘Hey boss, looking at my increased responsibilities and feedback from others, I feel I’m doing pretty well in my role. I’d like to ask you what I can do for you to earn a raise and in what time frame.’”
JJ recommended going into the conversation with a willingness to learn. “Be willing to ask ‘why’ if you’re denied,” he said.
Granting a raise may be a business decision, but the process is still a personal conversation. Don’t forget to treat it that way.
Jialing Xie, a Customer Success Manager, sums it up better than I could: “Be understanding — don’t flip because you don’t get what you want.”
This is about building your career, not burning bridges.
11 Tips for Successfully Navigating a Raise
Told you that you’d get a ‘quick tips’ section, didn’t I?
You might recognize some of these from above — they’re just so good I had to revisit them.
“Quantify and document your success.” (Kelly Venable)
“Give the person you’re asking for a raise the heads up. No one wants to be ill-prepared to have this talk.” (Keith Campagna)
“Data over emotion.” (Tim Davis)
“Be straightforward and direct.” (Matthew Peters)
“Be prepared with data when going into the conversation and know your plan B.” (Eva Poppe)
“Have your accomplishments outlined, written down, showing why you deserve a raise.” (Adam Holt)
“Ask about current goals for the year.” (Serena Chow)
“Don’t ambush your manager. Tell them you need their help on getting a raise.” (Macky Bradley)
“Do not wing it.” (Chirag Jay Patel)
“Be honest, be straightforward and understand your boss can’t just grant it. There’s a process that starts with you, and it ends up with a business decision.” (Alejandro Cabral)
“Demonstrate the mutual benefit, don’t make it one-sided. Know your bottom line: you have to be willing to walk away.” (Gia DeRose)
Have you successfully negotiated a raise? Are you looking to have that difficult conversation soon? Add your tips and questions to the community discussion below!
Good advice. I’ve found that in sales the best time to ask for a raise (or a stock bonus) is right before the new fiscal year starts, and after you can show strong results for that year. I received both a raise and stock bonus both years I was over 200% of plan.
Appreciate it, Ian. Also sounds like the best time to ask for a raise/bonus is when you’re 200% over plan!