How to Sell to Your Head of Sales


Nothing comes easy in sales — it’s always earned. But I’ve noticed a strange phenomenon: even the most seasoned and confident account executives can flinch when it comes to securing budget from their head of sales.


Reps won’t break a sweat asking for thousands of dollars from a future customer but second guess themselves when asking for a few hundred dollars from their boss for new software or a professional development seminar.


The hesitation to ask your boss for help on a project or pitch an idea to your executive can be detrimental to your quota and productivity. Part of the reason why 72% of sales teams (with fewer than 50 opportunities in their pipeline) don’t hit their revenue goals and 62% of a rep’s time is spent on the non-selling admin tasks is a lack of direct feedback from the front lines to Sales leadership.


So, I sought out expertise from Mixmax Head of Revenue Don Erwin, on the best ways to pitch a solution to your boss that will increase the likelihood the budget will get approved. Having led teams at Automil, HackerRank, and LinkedIn, Don has just about heard it all; and reveals his top tips below.


How to Ask Your Boss for Help on a Project


1. Do the research up front

It’s easy to get excited about new technology and want to share it with others. There’s a certain satisfaction in being an early adopter who’s “in the know.” However, with 850+ sales tools and 5000+ marketing technologies, it’s easy to get distracted by the new and shiny.


Ensure you’ve done your due diligence before pitching new technology. Have you test driven the solution? Scheduled a demo to better understand the capabilities and limitations?


Sending your boss a Slack message with a link to new technology you’ve just heard of and haven’t tried isn’t going to cut it. Whether you realize it or not, you’re placing the onus on them to research and evaluate the solution for you.


Instead, take the trial, speak to a rep, read reviews, and watch videos to better understand the strengths and drawbacks of the solution. Taking a trial or a demo will give you an idea of how easy or difficult it will be for your team to adopt the software.


2. Book some face time

Following Wu-Tang’s C.R.E.A.M. (cash rules everything around me) mantra, sales leaders naturally prioritize revenue initiatives with current and potential customers over internal items.


It’s likely your email or Slack message about internal process enhancements, while important, will get drowned out in the day-to-day volume — especially if introduced near quarter’s end.


Instead, create a dedicated time to meet and send an itemized agenda to keep the conversation focused, succinct, and quick to action steps. Face-to-face time ensures your voice is heard and the head of sales has dedicated time to evaluate your ideas.


3. Tie the solution to team goals or pain points

As a rep or SDR, you’ll likely be the end user of a product, like a dialer, prospecting tool, email automation software, or CRM. So, your evaluation of a tool is often based on the feature set. However, your head of sales is rarely — if ever — going to use the product they are evaluating for the team.


Describe how the solution helps with department goals, bottlenecks, or time management. For example, you might love the ability to insert your calendar availabilities for a meeting in an email because it saves three or four additional emails scheduling a demo with a prospect. However, your head of sales is unlikely to buy a tool just because it saves your inbox an email or two.


Relate the calendar scheduling feature to business impact or improvements in efficiency. This might sound like: “In our last sales quarterly, I noticed our demo booking rate going down significantly, I found this solution helped the team at Gong boost their meeting RSVP rates up to 41%, and believe it could be a good solution for us.


Not every tool or solution will present a clear ROI. In that case, track time saved. More time to sell leads to more realized revenue by the end of the quarter. You might say, “I tracked my time and found I spend four hours a week logging post-call activity and notes in our CRM. I found a great solution that does this automatically and can free up our team with an estimated ~20 more selling hours a week.


4. Create an upfront contract

With solution selling, if you haven’t established a champion or decision maker and defined clear steps towards success, there isn’t a real opportunity. The entire purchasing process is left up to the buyer’s whim.


The same goes for selling internally. If you haven’t established clear milestones for success, it’s likely your pitch will land on deaf ears when competing against other priorities.


Ensure you come up with mutually agreed upon milestones, such as:

  • What are the steps towards success?

  • What does your boss need to see before taking action?

  • What reservations do they have?

  • Should you meet all the criteria, when will they make a final decision?

Recap your discussions as you move between stages to ensure the upfront contract is understood. For example, “ After I showed you a demo and covered your concerns, we agreed to a decision on budget this month, are you still O.K. with that timeline? 


An upfront contract will move the conversation towards a decision and eliminate unforeseen reservations or delays.


5. Back everything up with data

While Sales leadership genuinely cares about employee satisfaction, they’re less biased towards action based on emotions alone. Sales is inherently performance based and inherently stressful.


The better you can articulate how a solution might impact performance — especially revenue — the stronger your positioning will be received. Before you can win your internal pitch, you need to ensure each of the following can be answered — with accompanying data:


  • Question: “Why [X] solution?

  • Example Answer: “ Mixmax’s sequences feature allow us to standardize our messaging and outreach across all teams and tweak individual email and call steps based on real-time performance. This process has led to an 18% increase in outbound performance.

  • Question: “Why now?

  • Example Answer: “ Our goal this quarter is to increase the total amount of opportunities by 40% without our SDR team adding more headcount. To do this, we need our outbound campaigns to bring in a higher amount of demo request conversions.

  • Question: “Why do anything? If we don’t make the change, what happens?

  • Example Answer: “Looking at the average demos booked from our outbound campaigns at the current rate, we’ll be XX% short of our Q3 goal. Without adding headcount, we must find a way to score more qualified demos from the same size of outbound pool — and this tool can help.


As Don put it, “If you can’t answer these questions, it’s a hope; a maybe, at best.”


6. Make it personal and tell a story

Rattling off dry features/benefits isn’t going to gain the attention of your head of sales; they get these pitches all the time. Instead, make it personal and help your boss better understand what it’s like at the front lines.


Package team goals, challenges, and day-to-day workflows into an entertaining story that shows a need for a solution — and how it can improve performance.


Finally, don’t forget to cover the ease of implementation. Your head of sales cares about the ramp period of any new tool and is constantly thinking, “Do we have time to implement this and still make our number?


Take these insights to heart. The difference between being a valued confidant versus a squeaky wheel is the ability to bring solutions to the table, not just reveal and complain about bottlenecks. Happy selling!