Raise the Stakes

One of the most stressful moments in our lives is asking for a raise.

Maybe you had a new baby.

Maybe it’s unexpected expenses.

Or maybe it’s just been years since you’ve seen your salary increase.

No matter if its receding margins, a volatile economy, or battling AI… gaining a pay raise is no small feat. Deciding to ask for a raise in the spur of the moment will never work to your advantage. And threatening to leave if you don’t get more money? Well… might as well clear out your login credentials now.

The good news is that it can be done. You just need to make sure you are strategic in planning and tactical in execution.

Plan Ahead (Way, Way Ahead)

According to recent surveys, the average stint of a software developer at a US company is less than 2 years.

That means by the time you are actually gearing up to ask for a raise, you are already switching jobs.

But what if you’re going to be there awhile? Well, time to start planning ahead.

Create a document which you track all the tasks, jobs, and accomplishments you complete throughout the tenure of the job. List everything you do from the routine parts of your day, to big projects, to the little last minute shit that gets dropped on your plate.

The point is, you want clear, quantifiable data of everything you’ve accomplished. When it’s documented, it becomes real and measurable, and makes it much harder to deny impact when it’s sitting right there on the page.

Oh, and color code it by type. Big projects, one color. Outside the job description, another color. That way you can look and honestly get a vibe check if you are truly going above and beyond, or you just are really good at your job.

Know the Market (and Keep Receipts)

We live in a data driven world. Access to statistical insights is easier than ever. Simply telling your manager “I deserve more”, while never was an effective strategy, these days it’s an even faster track to being blacklisted.

Using salary benchmarks from sources like Salary.com, glassdoor.com, or Levels.fyi can provide real life context to what peers in the same position and in the same locale.

This is simply invaluable data for you to determine not only how much you should ask for, but whether you should be asking for a raise in the first place.

Timing is Everything

Again, asking for a raise is a strategic affair. The more planning and care you put into it, the better set up you will be. If you have a strong relationship with your manager, being transparent and direct will be the fastest path to a real raise.

Communicate directly with your manager:

“I am really aiming to get earn a raise within the next 5-6 months. What can I do to help make that possible? Is there anything you need to see directly from me?”

This can accomplish two things.

1. It gives your manager direct insight into what your aspirations are. Maybe it requires a promotion or a certification, but including your manager can help give you roadmap to earning more money.

2. It will tell you if it’s not in the cards and you may need to look for a new job. Budgets might be an issue. Org charts or company acquisitions may be blocking a raise. But the sooner you know, the sooner you can make other plans.

Is it risky involving your manager? Definitely.

This approach really works well if you have a strong working relationship and feel you can be transparent.

But every manager on this planet knows that everyone is looking to earn more money, so this should never come as a surprise to them. Just make sure you feel like you are comfortable with opening up.

Upskill Like Your Job Depends on it (Probably Does)

Before you ask for more money, ask yourself:

“Have I grown professionally since my last raise?”

The fastest way in 2025 to increase your value is learning tools that align with your company’s evolving needs - especially around AI, automation, or data literacy.

Whether you master new AI tools to 10x your productivity, earn a certification in in cloud infrastructure, or learn how to prompt ChatGPT like a pro - showing initiative to stay ahead is powerful leverage to not only gain additional money, but insulate yourself against layoffs. Plus, those skills are highly desirable on the job market.

Confidence is Key (But so is Humility)

This is always the trickiest point to asking for a raise. You want to treat the process as a business conversation and not like you are asking for a favor. Position it as you helping the company win, not the company doing something nice for you.

In other words, focus on ROI, not emotion.

You have brought value to to the company, and it seems fair and reasonable to ask for a financial adjustment to reflect that along with the current market conditions and years of experience. You believe you truly deserve it and should act with confidence.

But here is the nuance. There is a thin line between confidence and arrogance and many people get it wrong. They come on too strong and all of a sudden an ask sounds more like a demand.

The way to temper that is by approaching with respect and humility. Creating a friendly, and approachable demeanor helps pull it all together. Most managers want to help you. Being likable is an important part of that. No manager likes to go to bat with leadership if they don’t feel like you are grateful.

Again, it’s such a nuanced balance between confidence, humility, and directness, that many people can fail just on nerves alone.

Practice with family, friends, anyone you trust that will provide you honest feedback

Remember, you got this.

New Lily Jobs

Here is a fresh batch of jobs for LATAM professional inside US companies

Business Intelligence Analyst

• 5+ years as a BA, preferably in a data-driven environment

• Strong proficiency in SQL for data extraction and manipulation

• Hands on experience creating reports and dashboards with Sigma Computing

• Familiarity with Snowflake, Redshift, or BigQuery

• $5,000 - $6,000 USD per month (Direct Hire)

PHP Developer

• 5+ years working in PHP development

• Experienced in using generative AI tools

• Short term project (6-8 weeks)

• Potential to stay on long term

• $25-$30 hour USD

Senior Data Engineer

• 5-8 years Data Engineering or Back-End development

• Strong experience in Python or Java

• Strong expertise in data modeling techniques

• Experienced in data warehouses (Snowflake, Redshift, or BigQuery)

• Bonus points for experience with Docker and/or Kubernetes

• $5,000- $6,500 USD (Direct hire)

If interested in any of these jobs, reach out directly to Tony Teshara on Linkedin.

Have a great week. Talk again with more hiring tips, interview techniques, and more jobs!

-Tony and Suzana