AMA: RocketReach VP, Sales, Michael A. Rosenberg on Developing Your Sales Career

My favorite to ask always starts with, "Tell me a story about..." The ending can be anything from professional to personal. Tell me a story about your proudest customer win. Tell me a story about a lost opportunity that you wished you won. Tell me a story about the last vacation you went on. Tell me a story about someone you stopped being friends with and why. For me it's not the answer, it's how you give the answer. In sales you need to be quick on your toes and engaging. Storytelling is the key to all of it.

I wish I could say there was a typical path but it is not often the case. If you were stay within the same company, and want to go the individual contributor (IC) track, you might view a typical career path to look something like: inbound SDR to outbound SDR to AE to Sr AE (or AM). If you were stay within the same company, and want to go the management track, it depends on what you are most interested in and the opportunities that are created. In the example above, you can stay as an SDR but move from Team Lead to Manager to Director to VP. But maybe you are promoted to an AE and then into management. If you switch companies, often times you can get into leadership more quickly if the company is smaller and/or a startup. When it comes to promotion the biggest chasms I see (the toughest jumps to make) are SDR to AE (never closing to closing) and IC to Manager (never leading officially, to leading and often times no longer producing).

In the end, the lagging indicators are what will justify a raise. They used to call it "earning your seat," referring to the physical seat you sit in. Within sales, you are either creating, winning, or keeping revenue, so those that can portray the most will typically get the increases and promotions. Now to get there is different and this is where leading indicators come in: who, when, how, and how often are you contacting who you need to in order to produce results. Successful sales reps can follow the formula in the most efficient way to produce results.

Strategy. That's the major difference between a Manager and Director. If you can operationalize strategy, that makes you a great manager. But if you can identify why things are or are not working, and know what to try and measure (creating a strategy), that's the makings of a great director. My steps are: 1. Have great data. Always be able to track what you are doing down to the smallest activity. The data should be measurements of success, both as a point-in-time and over a time period. This will tell you if something is working or not. 2. If things are or are not working, identify why. Is there something we can do more of? Is there something we should start or stop? 3. Test the theory. Put it into action, and as always, have data to measure what you do. When you see results trend positively, you picked a good strategy. Then start over and keep going! This is applicable in any role, any level, inside and outside of management.

1. Success of the product in the market, including renewal rates 2. Is it product led growth or sales led? PLG is usually preferred 3. How much turnover has there been? 4. What were and are the growth plans from a headcount perspective? 5. What's the track record of leadership? 6. Who supplied the funding and what are their goals with the company? 7. Is the communication style of your manager similar to yours? 8. Do the values of the organization line up with my own? 9. Are the benefits pertinent to me?

I see 2 different places that sales is headed: 1. Do more with less. Brute force (hiring more) used to be the answer to growing sales. Now the strategy is to load up the top reps, keep them busy, and get the best from them before we even think of hiring someone else. Sales efficiency is key from a profitability standard which is where the market is right now. 2. AI. Not saying the robots are coming for our jobs just yet, but with technology now that automates so many manual processes, is it so far fetched that in the next 5 years technology can tell us who to sell to, how to contact them, and write the email itself? What about AI images that talk and you don't realize that they are not actual people? Does it feel so futuristic to believe AI can dial or Zoom someone, respond based on what is said, overcome objections, negotiate pricing, and automatically send out order forms? There will always be a place for sales in some industries, especially emerging technologies where everything is new.

I avoid burnout in 3 ways: 1. Make your job easier by always having pipeline ready to go. Burnout is most common when a rep feels they need to start over, and then think that maybe they should just start over somewhere else. Always have good prospects to call, pipeline to win, or customers to contact and sell to. 2. Try new sales tactics, but don't stray too far from what has made you successful. Testing and trying new things is fun and spices things up, but do not overhaul your entire approach. Ask that one question you never do and see what happens. 3. Take time off. Salespeople can have major FOMO. I'm going to miss an inbound opportunity if I take off, I know it! If you follow #1 above, vacations, even small ones, will be your best friend. My first 10 years of working, 3 and 4 day weekends were my best ways to recharge!