\"What company should I join?\"

“What company should I join” should always be followed by “it depends”.

When I began my career in sales, I faced the challenge of finding the ideal company to work for.

Having assisted hundreds of individuals in their job search, I gained valuable insights into the key factors to help you make an informed decision.

Let's break down the process of choosing the right company.

Step 1

Startup vs. Big Name Company

One of the most common questions I receive is, "Should I choose a startup or a big-name company?" To help you consider your options, let's examine the pros and cons of each.

Startup Pros:

Startups offer an exhilarating, fast-paced environment. They often promise substantial equity, especially if the company goes public or is acquired, along with rapid career progression.

Working for a lesser-known company forces you to hone your sales skills, as you can't rely on name recognition. This skill-building is invaluable for long-term success.

Additionally, startups can provide more exposure to various company departments, helping you gain a broader understanding of business operations and develop complementary skills in a challenging environment.

Startup Cons:

On the flip side, startups can have a "grow or go" mentality, requiring immediate revenue generation and a lower tolerance for underperformance.

Sales development programs may not be as well-established, and promotions can stagnate if the company doesn't see revenue growth aka Account Executives (AEs) closing deals.

Clear career progression can be less evident in startups due to the absence of established timelines. In general, the future of a startup is uncertain; they can fail, and there are no guarantees.

However, if it pays off, the rewards can be generous and you can learn a lot in the process.

Now, let's consider the pros and cons of big-name companies.

Big Name Pros:

Recognizable names on your resume can open doors for the rest of your career. Future hiring managers won’t have to grill you to see if you’re qualified, a lot of trust comes with working at a big name like AWS, Oracle, Google, etc.

These companies typically offer more resources for professional development and often have well-defined sales programs, including comprehensive onboarding to ease the pressure on new hires.

Brand recognition may lead to higher response rates in cold calls and emails. For instance, receiving an email from a Dell representative is more likely to draw attention than one from Cupcake.io (making it up). Big companies can provide clear promotion timelines, offering a more stable career path with the proper performance.

These organizations not only attract top talent but also aim to retain it. Entry-level salespeople often have opportunities to explore roles in various departments such as campus recruiting, engineering, finance, or marketing, rather than being confined to sales.

And because the companies are large, there may be a lot of people getting onboarded with you to make the experience fun whereas a startup may be hiring people in a one-off fashion.

Big Name Cons:

Despite the benefits, there are drawbacks to working at big-name companies. They typically offer less equity and are known for their slower-moving corporate structures.

In some cases, employees may find themselves functioning primarily as salespeople, with limited involvement in broader company operations. I know a lot of people who feel like they can’t make an impact at a large company because the company is just so big.

The culture can be less innovative, and navigating through red tape can be challenging due to the organization's size.

Step 2

Product Is King

The product you sell significantly affects your compensation. Products with high-profit margins often result in higher pay (duh) so you have to find the one.

For instance, software sales, especially Software as a Service (SaaS), typically yield higher margins because you're essentially selling thin air (digital product), minus software engineering costs.

But there is also hardware (like I sold at Dell).

The margins on data center products are high, so it’s a lucrative product to sell. But if you enter Dell and sell laptops, there is less margin and it may be less lucrative in terms of compensation.

It's important to determine whether the product you're selling is a want or a need. In most cases, companies position their product as a “must-have” rather than a “nice-to-have.” But trust me, when the economy shrinks, spending will focus on needs, not wants.

Therefore, products that fulfill essential requirements are crucial.

Ex #1: Companies need to store data, their most valuable asset in a recession or not. If they don’t they are at major risks. They would have to delete data and sacrifice repercussions because of that. It’s a core technology need the business will always have and why on-premise and cloud data storage are huge industries. This is a “need” product for most.

Ex #2: You sell a cool SaaS calendar that has fancy integrations and because it’s SaaS the margins are amazing and they can pay reps great. But because there are so many competitors and companies don’t need all the fancy bells and whistles, you may have trouble selling in a recession when spending cuts back and companies are only purchasing necessary tools to keep the lights on.

The product you sell is king. There is no right or wrong answer, just awareness of what you are signing up for.

Step 3:

Your Best Fit

The choice between startups, big-name companies, and products you sell should align with your risk tolerance, goals, and career preferences. Consider the game you’re playing and ask yourself, what am I optimizing for?

- Competitive pay

- Work-life balance

- Fully remote work

- Rapid promotion to Account Executive (AE)

- Passion for the product

- Alignment with the company's mission

- Training and development

- Name recognition

- Skills

There’s no right answer and you can optimize for things at different points in your career. When I first started, I opted for name recognition with good training and development.

I figured if I could build skills it would make me more attractive to employers if I want to take a risk later to join a startup with lots of upside.

Regardless, It's crucial to align your choices with your genuine aspirations and be honest with yourself.

Step 4

(Bonus): Evaluating a Startup

Evaluating the strength of a startup involves assessing various aspects of the company's operations, team, and market positioning. Here are some key factors to consider when evaluating a startup:

Team: Assess the experience and track record of the founding team. Look for members with relevant industry expertise, successful startups, or a strong professional background. Check if the team has a clear vision and mission for the company.

Market: Evaluate the size and potential of the target market. Is it large enough to support the startup's growth? Consider the startup's market positioning and its unique value proposition. Is there a clear market need for the product or service? Examine the competitive landscape to understand who the key competitors are and how the startup differentiates itself.

Product/Service: Assess the quality and uniqueness of the product or service. Does it solve a real problem or offer a compelling solution? Consider the stage of development (e.g., prototype, beta, production-ready) and the timeline for product launch. Look for feedback from early customers or beta testers.

Traction: Check if the startup has gained any traction in terms of user adoption, revenue, or partnerships. Evaluate growth metrics such as customer acquisition rate, retention, and revenue growth.

Business Model: Understand the startup's revenue model. How does it plan to monetize its product or service? Analyze the pricing strategy and whether it's sustainable and competitive.

Funding: Review the startup's funding history. Has it received funding from reputable investors or venture capital firms? Examine the current financial health and runway (how long the startup can operate with its existing funds).

Market Fit and Validation: Look for evidence of product-market fit, such as positive customer feedback, user engagement, or high Net Promoter Scores (NPS). Consider any validation from industry experts, awards, or partnerships.

Exit Strategy: Understand the startup's long-term goals. Does it plan to be acquired, go public, or remain independent? Assess the potential for an exit and the implications for investors.

Risks and Challenges: Identify and assess the risks and challenges the startup may face, such as market competition, technology risks, or regulatory hurdles.

Network and Connections: Consider the startup's network and connections within the industry, including mentors, advisors, and partnerships.

I look at a few things:

1. Who’s funding it? Based on the companies backing it, I see if they have a track record of investing in winners. If so, it’s typically a good sign.

2. Gather insights from industry professionals (preferably non-employees). Get a non-biased take on how others not in the company view its potential.

3. Check out employees on Linkedin and see where they came from. I know a lot of people who jump from IPO to IPO and can rinse and repeat the success they had at a startup.

Ultimately, the decision of which company is right for you is personal, and no one can answer it better than you. Armed with these frameworks, you'll be equipped to make the best decision for yourself.