Mastering B2B sales with Philip Olesch

The Prospecting Masterclass ep. 22

Hey there Croners! Our journey into the depths of Sales never stops, here with episode 22 of The Prospecting Masterclass, the original Crono column that gives you insights and tips right from the best minds in sales.

In the following episode, we’ll get through Philip Olesch‘s experience and tips to improve your B2B sales game. Not only that, but his reflection on taking pauses and avoiding rush on the job will inspire you even more.

Enjoy reading the interview!

Hey Philip, let's start with 5 words to describe yourself!

Positive, Structured, hands-on Sales Builder

Philip's career from Outbound to Consulting

Philip has been involved in B2B Sales for around 9 years: his career in Outbound Sales began at Google, where he worked as a Full Cycle Seller, driven by curiosity to explore the inner workings of one of the world’s largest companies. Later, that same curiosity led him to join forces with SalesCloud, where Philip has been collaborating with over 25 startups to grow their revenue.

Within SalesCloud, he has taken on various roles in different Sales Organizations, supporting as an SDR, AE, Team Lead, and also in more Enablement-focused positions before moving into his current role with a more strategic focus.

As a Senior Sales Unit Building Consultant, he’s responsible for delivering consulting services to clients. This means Philip enables founders and sales leaders to build up their Sales Organization into a predictable and scalable revenue engine.

Or like he explained to us “Imagine having a Co-Pilot that helps you oversee priorities, shares knowledge for upcoming challenges, and reviews dashboards with you to ensure you are still heading in the right direction and have all passengers on board.”

What challenges have you faced in your past and current professional experiences? How did you overcome them?

Starting in Sales it was mostly about having enough time to do sales in high volume and still improve myself, as there was not much training around. So managing your pipeline in Full Cycle Sales, while closing deals, improving your pitches and messaging and discovery, and still reaching targets.

Three things helped me the most:

  1. Metrical understanding of Sales, meaning how many new leads one needs to touch regularly for a healthy pipeline, how many to have in the Proposal stage etc to keep up with targets and not have highs and lows all over your funnel.

  2. Consistency and planning help you to achieve incredible things. Ensure to execute specific things at certain reserved times, and block the required amount of time so nothing can prevent you from getting these done. Working repeatably on bigger tasks makes it achievable.

  3. Structured working for repeatability and iterations. Following the same approach regularly to being able to compare results and then changing things to repeat helps you to figure out your message market fit. May it be in your initial pitch (from lead to meeting) or later in your discovery and the following proposal.

In my consulting role and as a Sales leader it was initially tough to handle all responsibilities and priorities.

Here it helped me to force myself to stop, take a quick break and review priorities and urgencies of all my To-Dos to get them in the best order. Additionally getting clients to set their priorities right when fighting through day-to-day work and obstacles was challenging at first.

Repeatedly forcing them to pause in between their desire to rush from personal issues 1 to 2 works well for me. Always going back to the big picture, helping them to zoom out and focus on their midterm goals and to plan actions towards this often will also eliminate the operational short-term topics.

What are the most remarkable lessons you've learnt as a sales?
  • Honesty, transparency and relationship-building always pay off. Even if you might lose deals through it initially, this is best for your revenue in the long run.
  • Pausing or taking breaks helps you not only to recover but also to zoom out and challenge yourself for improvement. This makes it even more important.
  • Make all your messaging value-based = make it about the customers and “what’s in it for them”.
How do you see B2B outbound sales changing in the next 12 months? What challenges and trends do you anticipate?

AI usage will grow further and lead to a wave of personalization at scale, but most likely still not on the highest levels. This will lead to more flooded inboxes in mail and social.

Most likely email will still be channel No 1 in 2024, but will perform worse and worse.

Thus LinkedIn will be the most used channel for cold outreach end of next year. I assume the return of cold calling will still take some time, as a high share of Salespeople tends to avoid this.

For all channels to perform you need to excel at the highest level and deliver high value and messaging to your clients upfront. This will become more and more important this year.

What I am hoping for is that more and more Sales organizations and Sellers will upskill and focus more on value-adding messaging, solution selling and buyer-centric approaches.

What advice would you give someone starting today in the B2B Sales industry?
  1. Get a buyer-centric sales approach and believe in solution selling and bringing value for your clients.
  2. Learn what’s factors for great messaging, eg. Emails, Web, Linkedin, Calls, etc.
  3. Understand the metrical game within sales to find your way to your target.
  4. Learn how to use AI to automate the basic repetitive work you’re facing. Without this other reps will be far more productive than you and hence ahead in terms of performance.

To keep it short:

For Prospecting: Master tools and AI usage as well as learn how to craft great emails and messages.

For Closing: Learn how to quantify pain well in your discoveries for a higher chance (any chance?) in closing.

Subscribe to get Bolt ⚡️

* indicates required

Please select all the ways you would like to hear from Crono:

You can unsubscribe at any time by clicking the link in the footer of our emails. For information about our privacy practices, please visit our website.

We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing. Learn more about Mailchimp's privacy practices.

Sign Up Form

Subscribe to get Bolt ⚡️

* indicates required

Please select all the ways you would like to hear from Crono:

You can unsubscribe at any time by clicking the link in the footer of our emails. For information about our privacy practices, please visit our website.

We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing. Learn more about Mailchimp's privacy practices.

⚡️Bolt - The B2B Sales newsletter by Crono

Subscribe to our newsletter to receive monthly updates and insights on the future of B2B Sales!