Hiring your first sales rep: 10 tips and common mistakes

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How many times have you been at an event and met someone who gave you the pitch “I have this great idea, I just need someone to build it for me” or some variation of that?

This has become such a cliche in startup circles that it’s almost cringe-worthy. If all someone has is an idea then they’ve basically got nothing. As the old Edison quote goes “genius is one percent inspiration and ninety-nine percent perspiration.”

That being said, the other side of this pitch doesn’t get a ton of attention even though the problem is just as common.

There are lots of startups that build pretty solid products but never end up getting traction because they don’t figure out the sales and marketing side of things.

You don’t see a lot of technical founders searching for business development help, mostly because many engineers don’t even know they have a problem. They spend a year in their basement building the most amazing solution to a problem nobody has. When they do finally surface they discover that 6 of the 10 assumptions they made were wrong, and usually give up soon thereafter.

I’m an engineer, and I’ve seen this problem come up first hand. One of the most basic ways to avoid it is to start focusing early on customer validation. What that means in the most basic terms is to not write a single line of code before you talk to a few dozen customers who tell you unequivocally that they will buy the thing you’re thinking of building.

As you talk to customers tweak the pitch until you have 9 out of 10 potential customers telling you that they will pay money for what you’re planning to build (hint: 8 of them are lying.) This is your first step towards developing a sales process.

You (or your co-founder) need to learn to sell. Frankly, it’s not that hard and it’s mostly about persistence when it comes to getting a few pilot customers – they’re going to be early adopters, they won’t expect a polished sales pitch. It’s essential that this basic sales and marketing expertise lie within the core team. Which brings me to the first tip about hiring your first sales reps:

1. Learn how to sell and develop a basic process.

The most common mistake technical startup founders seem to make is to try and cop out on the sales part of the business. They feel they don’t know how to sell and are worried that people won’t take them seriously because they don’t have grey hair. So they hire an experienced sales guy (a friend of a friend,) give him ownership of all sales and just sit back and wait for the deals to flow in. It seems like such a plausible idea (it’s exactly what I did with Top Hat Monocle) and yet I’ve never once seen it work out. You need to learn to sell. It’s actually a skill very similar to raising money, so it’s something you’ll need to do anyway. Learn to sell just well enough to close the first few customers and develop a basic process that you can plug someone into.

2. Find reps who have experience with the same deal size and sales cycle as your product.

If your product costs $200 per month and has a 1-2 week sales cycle, don’t hire some with enterprise experience who’s used to closing three $500k deals a year, it won’t work out. A match on deal size and sales cycle is probably the best predictor of whether the rep will be a good fit.

3. Experience within your industry is useful but not essential if your product isn’t too complex.

Focus on item 2 above. Unless you’re selling a very complex product with a long (6 month+) sales cycle, don’t worry about industry experience.

4. If it’s a technical sale, tech savvy matters.

Don’t hire someone who barely knows how to use a computer to sell a software product. Frankly in general you should only hire people with basic technical literacy because otherwise you will be explaining to them how to use the CRM and your webinar software 5 times a day.

5. Sales reps are great bullshitters – ignore their words.

Only look at verifiable track record to assess the rep. This means getting a printed record of their quota attainment at every sales job they’ve had, then verifying that record with their supervisor. Anyone who hasn’t consistently blown away their quota at every job is a risk.

6. Place minimal value on prior contacts and rolodex.

The rolodex runs out after about two weeks. After that it’s all about prospecting and hard work. Don’t ever overlook a lack of experience or cultural fit because you feel the rep has a rolodex of clients they claim they’ll bring with them (they’re probably exaggerating anyway, see #5 above.)

7. With personality, focus on work ethic and motivation.

Sales is repetitive hard work. When hiring reps look for work ethic and drive. Look for people who need to earn a certain amount of money to maintain their lifestyle due to financial obligations – a big mortgage is the best motivator to hit quota.

8. Over time start to specialize your sales team.

Lead generation and research. Appointment setting. Follow ups and closing. Each is a separate role. You should segment by task and eventually by customer size or market. It may not even take that long for it to make sense to do this – we started specializing at Top Hat Monocle when we had just 3 reps.

9. Sales reps will maximize their paycheque above all else.

At least the good ones will. You need to ensure your compensation plan incentivizes sales and has relatively short term rewards. This typically means at least 50% of overall earnings should be from commission and there should be a monthly performance based commission payout. Don’t try to hire people on 100% commission, because you will likely only attract flakes who waste your time and never deliver.

10. Metric everything. Obsessively.

How many calls per day does each rep make. How many emails. What is the conversion rate on email responses. How many meetings does each rep go on per day. How many inbound leads are being generated. What is the time from inbound lead to follow-up. How many foliow-ups does each rep do per day. What is the mean time between follow ups. Everything. Metric everything.

Hiring a Growth Hacker on StartupNorth.ca

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Did you know that we run a job board for startups? It does allow companies to reach an audience that is interested in startups.

“Amar joined us 3 weeks ago after a long trial of hunting down and applying for the “Growth Hacker” position we posted on StartupNorth. We couldn’t be happier with his progress, hunger and efficiency. Over to you Amar!” – Michael Litt, Vidyard

There are great stories of people find companies and roles like Amar Chahal (LinkedIn) and the Growth Hacker role at Vidyard. If your a looking for a new gig, go read about how Amar was hired at Vidyard. It will blow your mind how much he committed to the process. I’m actually shocked that no one has socially hacked our job board as a candidate, i.e., it’s not that expensive but you could pay to highlight your resume or portfolio, because it will only work once.

Post Your Job

Postings are only $25 for 60 days. Postings are embedded on StartupNorth.ca and all postings are shared on our Twitter account. For example:


New job posted: Technical Marketer / Maintenance Assistant Inc / Toronto, ON, Canada http://t.co/WQkBUV6v
@startupnorth
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It’s a quick, relatively inexpensive way to post jobs to a targeted audience. Get a little bit of distribution and hopefully find candidates like Amar.

We are open to discussion about how we can improve the Jobs Board for both candidates and companies. Got a suggestion for how we improve things? We are all ears.

Looking to get hired by a startup? 10 ways to stand out

Editor’s Note: This is a guest post by Bruce Dorland (LinkedIn, @brucedorland). Bruce is the Managing Director & Recruiter at Grossman Dorland Recruiting. gdR recruits for permanent and contract positions at all levels, from roles for talented young professionals to accomplished executives. Prior to founding gdR, Bruce spent time at Brightspark, Tucows shipping products that have been used by over 3MM users.

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Occasionally I interview a developer that really impresses me with their ability to make their profile come to life beyond their resume.

Want to know what makes these developers stand out? Here are my top ten tips for making a big impression. Many of these tips work for both a resume and, once that stellar resume gets you in the door, a job interview.

I think developers looking for a new job can have it tough. Many, if not most, job descriptions aren’t great at describing the actual nature of the role. Traditional resume formats can be flat. Interviewers don’t always ask effective questions, and HR departments that rely heavily on keyword matching can’t differentiate you qualitatively from other candidates.

The result: unless you do something different, the odds of standing out are stacked against you. But if you’re trying to get into a startup or midsize tech company that is truly looking to build a top-notch team, it’s essential that you learn to make your mark. Here’s how:

Tip #1: Show me your side projects

Small and midsize companies increasingly value a well-rounded candidate with a passion for technology and a dedication to growing their technical skillset. For confidentially reasons it can be hard to show people the code you’ve been working on at your job, but side projects are a great way to show how you design and implement code. In my opinion, side projects are also a surefire sign of your passion for the craft.

A great tool for this is a code sharing and publishing platform like GitHub. The site gives you a place to contribute to open source projects and build a public reputation for your work since the community is quite transparent. For instance, if a patch you submit is accepted, you get credit for it and it shows up in your profile. The site acts like a resume that helps the maintainer of a project determine your reputation.

Tip #2: Have a relevant and up-to-date portfolio site

While it’s common for certain types of developers to have a portfolio site, UI developers in particular, I’ve found that many create a site early on in their career but don’t keep it up to date.

Most employers who refer to your portfolio site won’t necessarily have the time or patience to fill in any blanks or realize is something is out of date. It’s up to you to make sure that your site accurately reflects where your skill level is today, that sites that aren’t live anymore are removed, that screenshots are illustrative and relevant, and that you give the context of why your work was original or important at that time.

Tip #3: Form your own opinions on technology

What are the topics of the day within your company? What technologies have they chosen to use and why? Form an opinion about your current company’s choices of tools and have an opinion about where things might be going in the future (of course, you’ll want to make sure you’re observing confidentiality requirements if you intend to share this information in an interview).

In addition, know the big discussions happening in tech today. What are the latest thoughts on Continuous Integration and Deployment options? Javascript MVC frameworks? Big data? Be knowledgeable and you’ll always be ready if asked for your thoughts on the trends shaping your field.

Tip #4: Understand the users and business behind your product

Many developers are used to only describing their products from a tech perspective out, rather than a user perspective in.

To make yourself stand out from the crowd, be able to articulate who the users of your product are and the solution it provides for them, and more generally, the business side of the product.

Go into an interview from this angle in mind and a company will be confident that you always do your work with the user in mind.

Tip #5: Whiteboard your work

Many developers aren’t used to talking about themselves, their product architecture, what they’ve accomplished, or how to best articulate the technical challenges they faced. This is why whiteboarding your work is so important.

When I say whiteboarding, I mean mapping out the architecture of your product, the modules your were responsible for and the technological challenges you faced. It’s about taking all this information and putting it into words so that you can talk about it during an interview.

This might also literally mean drawing this all out on a whiteboard, as I often ask candidates to do during an interview. You can’t lie to yourself or anyone else in front of that whiteboard – either you can map out and explain your work, or you can’t.

If you can bring sample documents to reinforce your whiteboard map without breaking confidentiality agreements, that helps too.

Tip #6: Make it interactive – demo your work!

In an interview, I’m always much more engaged if a developer can demo their product for me. This might seem obvious, but you’d be surprised how seldom I’m asked if I want a live tour of the product they’ve been working on.

If you worked for a SaaS company, for example, and you still have an account, offer to log in and show me around. Tell me which modules you were responsible for. This is always much more visual and stimulating than a written summary of your work.

Tip #7: Be articulate, simple & concise.

Once you’ve prepared your whiteboard, be prepared to articulate all this information (your skills, your current responsibilities and your product) in a simple, concise manner. Start with less detail and drill down where appropriate. If you don’t know how deep to go, just ask the interviewer if they want to know more.

Be prepared to guide some of the questioning so you know the interviewer is getting all the information that makes you an appealing candidate. An interview is an interactive process, after all.

Tip #8: Tell me what you find exciting in tech today.

Even if you haven’t been working for the sexiest company, products or applications, always be prepared to talk about what you DO admire and why.

Please do me a favour – don’t say Apple or Google (and definitely don’t say Microsoft!). Come up with unique ideas that reflect your professional opinions on what makes a product or service shine.

Tip #9: Get to know the company you’re interviewing for.

Obvious, right? But it can speak volumes if a candidate isn’t informed, which happens a lot.

Find out what technology stack the company uses and review their FAQs, support forums, training guides and blog. If they have a free trial account of their product, sign up for an account and give it a test drive. The more you know, the more enthusiastic you’ll appear and the better and more useful your own questions will be.

Tip #10: Come to the interview with great questions.

Hopefully after having done all the research I’ve suggested, you’ll have some original questions to ask that not only show that you’ve come prepared, but that will also help you make a decision about how the company, product, technology and team fit your overall career goals.